{"id":47436,"date":"2023-11-04T08:00:31","date_gmt":"2023-11-04T00:00:31","guid":{"rendered":"\/\/www.gsbet888.com\/?p=47436"},"modified":"2023-11-02T19:15:10","modified_gmt":"2023-11-02T11:15:10","slug":"%e5%a4%a9%e7%84%b6%e4%ba%a7%e7%89%a9-heilonine%e7%9a%84%e5%85%a8%e5%90%88%e6%88%90","status":"publish","type":"post","link":"\/\/www.gsbet888.com\/%e5%8c%96%e5%ad%a6%e6%9d%82%e8%ae%b0\/recentpaper\/2023\/11\/%e5%a4%a9%e7%84%b6%e4%ba%a7%e7%89%a9-heilonine%e7%9a%84%e5%85%a8%e5%90%88%e6%88%90.html","title":{"rendered":"\u5929\u7136\u4ea7\u7269(+)-Heilonine\u7684\u5168\u5408\u6210"},"content":{"rendered":"<p style=\"text-align: justify;\"><strong>\u4f5c\u8005\uff1a\u77f3\u6cb9\u919a<\/strong><\/p>\n<h4 style=\"text-align: justify;\">\u5bfc\u8bfb\uff1a<\/h4>\n<p style=\"text-align: justify;\">\u8fd1\u65e5\uff0c\u829d\u52a0\u54e5\u5927\u5b66\u7684Viresh H. Rawal\u6559\u6388\u56e2\u961f\u5728<em>J. Am. Chem. Soc.<\/em>\u4e0a\uff0c\u4ee5 \u201cEnantioselective Total Synthesis of (+)-Heilonine\u201d\u4e3a\u9898\uff0c\u4ee521\u6b65\u9996\u6b21\u5b8c\u6210\u4e86(+)-Heilonine\u7684\u5168\u5408\u6210\u3002\u5176\u4e2d\uff0c\u5173\u952e\u6b65\u9aa4\u4e3b\u8981\u6d89\u53ca: Rh\u50ac\u5316\u7684[2+2+2]\u73af\u5316\u5f02\u6784\u5316(Rh catalyzed [2 + 2 + 2] cycloisomerization reaction); \u4e0d\u5bf9\u79f0Diels\u2013Alder\u53cd\u5e94 (asymmetric Diels\u2013Alder reaction ); Robinson\u73af\u5316 (Robinson annulation)\u7b49\u3002<\/p>\n<blockquote><p>\u201cEnantioselective Total Synthesis of (+)-Heilonine<\/p>\n<p>Kyle J. Cassaidy and Viresh H. Rawal*<\/p>\n<p><em>J. Am. Chem. Soc.<\/em>, <strong>2021, <\/strong><em>143<\/em>, 16394\u201316400. doi: <a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/jacs.1c08756\">10.1021\/jacs.1c08756<\/a>\u201d<\/p><\/blockquote>\n<h4 style=\"text-align: justify;\">\u6b63\u6587\uff1a<\/h4>\n<p style=\"text-align: justify;\">\u753e\u4f53\u751f\u7269\u78b1\u56e0\u5176\u72ec\u7279\u7684\u9aa8\u67b6\u548c\u7279\u6b8a\u7684\u751f\u7269\u6d3b\u6027\u5f15\u8d77\u4e86\u4f17\u591a\u79d1\u5b66\u5bb6\u5e7f\u6cdb\u7684\u5173\u6ce8<sup>[1]<\/sup>\u3002\u4ece\u767e\u5408\u79d1\u85dc\u82a6\u5c5e\u690d\u7269\u4e2d\u5206\u79bb\u5f97\u5230\u85dc\u82a6(Veratrum)\u751f\u7269\u78b1\u5c31\u662f\u5176\u4e2d\u4e4b\u4e00\u3002\u4ece\u7ed3\u6784\u4e0a\u770b\uff0c\u85dc\u82a6(Veratrum)\u751f\u7269\u78b1\u5177\u6709\u5171\u540c\u7684C-nor-D-homo\u753e\u4f53\u9aa8\u67b6\uff0c\u800c\u6839\u636e\u5176\u4e0e\u54cc\u5576\u73af(F\u73af)\u7684\u8fde\u63a5\u65b9\u5f0f\u53ef\u5206\u4e3a\u4e09\u7c7b\uff1acevanine\u578b\u3001veratramine\u578b\u548cjervine\u578b\uff08Figure 1\uff09<sup>[2]<\/sup>\u3002Heilonine (1)\u5c31\u662fcevanine\u578b\u751f\u7269\u78b1\uff0c\u5176\u662f\u7531\u65e5\u672c\u79d1\u5b66\u5bb6Koh Kaneko \u6559\u6388\u53ca\u5176\u540c\u4e8b\u4e8e1989\u5e74\u4ece\u9ed1\u9f99\u6c5f\u7701\u767e\u5408\u79d1\u690d\u7269\u5e73\u8d1d\u6bcd<em>Fritillaria Ussuriensis Maxim.<\/em>\u4e2d\u5206\u79bb\u83b7\u5f97 (Figure 1)<sup>[3]<\/sup>\uff0c\u5e76\u4e14\u5176\u88ab\u8ba4\u4e3a\u662f\u91cd\u8981\u7684\u4e2d\u8349\u836f\u201c\u8d1d\u6bcd\u201d\u7684\u6210\u5206(\u4f20\u7edf\u4e2d\u533b\u4e2d\u7528\u6765\u9547\u9759\u3001\u6b62\u54b3\u548c\u795b\u75f0)<sup> [4]<\/sup>\u3002\u6b64\u5916\uff0cKoh Kaneko \u6559\u6388\u901a\u8fc7\u901a\u8fc7NMR\u548cX\u5c04\u7ebf\u6676\u4f53\u5b66\u5206\u6790\u9610\u660e\u4e86\u5176\u5177\u6709\u590d\u6742\u516d\u73af\u7ed3\u6784\u548c\u4e5d\u4e2a\u7acb\u4f53\u4e2d\u5fc3\u3002\u8fd1\u65e5\uff0cViresh H. Rawal\u6559\u6388\u56e2\u4ee521\u6b65\u9996\u6b21\u5b8c\u6210\u4e86(+)-Heilonine\u7684\u5168\u5408\u6210\uff0c\u5e76\u53d1\u8868\u4e8e<em>J. Am. Chem. Soc.<\/em>\u4e0a\u3002<\/p>\n<p style=\"text-align: justify;\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-47438 size-full\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2023\/11\/image003-1.jpg\" alt=\"\" width=\"1269\" height=\"658\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2023\/11\/image003-1.jpg 1269w, https:\/\/assets.www.gsbet888.com\/uploads\/2023\/11\/image003-1-300x156.jpg 300w, https:\/\/assets.www.gsbet888.com\/uploads\/2023\/11\/image003-1-680x353.jpg 680w, https:\/\/assets.www.gsbet888.com\/uploads\/2023\/11\/image003-1-768x398.jpg 768w\" sizes=\"(max-width: 1269px) 100vw, 1269px\" \/><\/p>\n<p style=\"text-align: justify;\">\u9996\u5148\uff0c(+)-Heilonine (<strong>1<\/strong>)\u5177\u6709\u590d\u6742\u7684\u516d\u73af\u7ed3\u6784\u4ee5\u53ca9\u4e2a\u7acb\u4f53\u4e2d\u5fc3\u3002\u57fa\u4e8e\u4e0a\u8ff0\u9aa8\u67b6\uff0c\u4f5c\u8005\u5bf9(+)-Heilonine (<strong>1<\/strong>)\u8fdb\u884c\u4e86\u76f8\u5173\u7684\u9006\u5408\u6210\u5206\u6790(Scheme 1)\u3002\u5373\u4ee5\u919b<strong>G<\/strong>\u548c\u70ef\u9187\u7845\u919a<strong>F<\/strong>\u4e3a\u539f\u6599\u7ecf\u4e0d\u5bf9\u79f0Diels-Alder\u73af\u52a0\u6210\u83b7\u5f97\u516d\u5143\u73af<strong>E<\/strong><strong>\uff0c<\/strong><strong>E<\/strong>\u7ecfRobinson\u73af\u5316\u5f97\u5230\u780c\u5757\u53cc\u73af\u4e8c\u7094<strong>C<\/strong><strong>\u3002<\/strong>\u53e6\u5916\u4e00\u4e2a\u780c\u5757\u54cc\u5576\u916e<strong>D<\/strong>\u53ef\u7531\u4e19\u9170\u5316\u5408\u7269<strong>H<\/strong>\u548c\u919b\u7ecf\u4e0d\u5bf9\u79f0Evans aldol\u53cd\u5e94\u4ee5\u53ca lactamization\uff08\u5f15\u5165N\uff09\u5408\u6210\u3002\u53cc\u73af\u4e8c\u7094<strong>C<\/strong>\u548c\u54cc\u5576\u916e<strong>D<\/strong>\u4e3a\u539f\u6599\u7ecf\u70f7\u57fa\u5316\u53cd\u5e94\u5f97\u4e2d\u95f4\u4f53<strong>B<\/strong>\uff0c<strong>B<\/strong>\u901a\u8fc7Rh\u50ac\u5316\u7684[2+2+2]\u73af\u5316\u5f02\u6784\u5316\u5408\u6210\u5173\u952e\u780c\u5757<strong>A<\/strong><sup>[5]<\/sup>\u3002\u6700\u540e\uff0c\u5173\u952e\u4e2d\u95f4\u4f53<strong>A<\/strong>\u901a\u8fc7\u975e\u5bf9\u6620\u9009\u62e9\u6027\u7532\u57fa\u5316\u548c\u6c27\u5316\u53cd\u5e94\u5b8c\u6210(<strong>1<\/strong>)\u7684\u5168\u5408\u6210\u3002<\/p>\n<p style=\"text-align: justify;\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-47439 size-full\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2023\/11\/image005-1.jpg\" alt=\"\" width=\"1269\" height=\"489\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2023\/11\/image005-1.jpg 1269w, https:\/\/assets.www.gsbet888.com\/uploads\/2023\/11\/image005-1-300x116.jpg 300w, https:\/\/assets.www.gsbet888.com\/uploads\/2023\/11\/image005-1-680x262.jpg 680w, https:\/\/assets.www.gsbet888.com\/uploads\/2023\/11\/image005-1-768x296.jpg 768w\" sizes=\"(max-width: 1269px) 100vw, 1269px\" \/><\/p>\n<p style=\"text-align: justify;\">\u9996\u5148\uff0c\u8be5\u5c0f\u7ec4\u5408\u6210\u4e86\u780c\u575717\u548c26\uff0c\u5982Scheme 2, 3\u3002<\/p>\n<p style=\"text-align: justify;\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-47440 size-full\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2023\/11\/image007-1.jpg\" alt=\"\" width=\"1269\" height=\"660\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2023\/11\/image007-1.jpg 1269w, https:\/\/assets.www.gsbet888.com\/uploads\/2023\/11\/image007-1-300x156.jpg 300w, https:\/\/assets.www.gsbet888.com\/uploads\/2023\/11\/image007-1-680x354.jpg 680w, https:\/\/assets.www.gsbet888.com\/uploads\/2023\/11\/image007-1-768x399.jpg 768w\" sizes=\"(max-width: 1269px) 100vw, 1269px\" \/> <img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-47447 size-full\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2023\/11\/c5f2025c908dc07244740f52bf20f2c5.png\" alt=\"\" width=\"664\" height=\"279\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2023\/11\/c5f2025c908dc07244740f52bf20f2c5.png 664w, https:\/\/assets.www.gsbet888.com\/uploads\/2023\/11\/c5f2025c908dc07244740f52bf20f2c5-300x126.png 300w\" sizes=\"(max-width: 664px) 100vw, 664px\" \/><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-47453 size-full\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2023\/11\/877450e351b6c1824665eac9c2ddc472.png\" alt=\"\" width=\"501\" height=\"620\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2023\/11\/877450e351b6c1824665eac9c2ddc472.png 501w, https:\/\/assets.www.gsbet888.com\/uploads\/2023\/11\/877450e351b6c1824665eac9c2ddc472-242x300.png 242w\" sizes=\"(max-width: 501px) 100vw, 501px\" \/><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-47448 size-full\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2023\/11\/e937d46a4e0b4c37ca5a65d6709ae75c.png\" alt=\"\" width=\"569\" height=\"225\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2023\/11\/e937d46a4e0b4c37ca5a65d6709ae75c.png 569w, https:\/\/assets.www.gsbet888.com\/uploads\/2023\/11\/e937d46a4e0b4c37ca5a65d6709ae75c-300x119.png 300w\" sizes=\"(max-width: 569px) 100vw, 569px\" \/><\/p>\n<p style=\"text-align: justify;\">\u8be5\u5c0f\u7ec4\u5b8c\u6210\u4e86Vilmoraconitine (<strong>3<\/strong>)\u7684\u5408\u6210\u8def\u7ebf\u8bbe\u8ba1\uff0c\u5982Scheme 4\u3002<\/p>\n<p style=\"text-align: justify;\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-47452 size-full\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2023\/11\/ab6c6860eabe8a29f3bf36d3dabb5d1c.png\" alt=\"\" width=\"1024\" height=\"777\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2023\/11\/ab6c6860eabe8a29f3bf36d3dabb5d1c.png 1024w, https:\/\/assets.www.gsbet888.com\/uploads\/2023\/11\/ab6c6860eabe8a29f3bf36d3dabb5d1c-300x228.png 300w, https:\/\/assets.www.gsbet888.com\/uploads\/2023\/11\/ab6c6860eabe8a29f3bf36d3dabb5d1c-680x516.png 680w, https:\/\/assets.www.gsbet888.com\/uploads\/2023\/11\/ab6c6860eabe8a29f3bf36d3dabb5d1c-768x583.png 768w\" sizes=\"(max-width: 1024px) 100vw, 1024px\" \/><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-47449 size-full\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2023\/11\/4d640dda86099ae6090df5d9cafb2f4b.png\" alt=\"\" width=\"661\" height=\"289\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2023\/11\/4d640dda86099ae6090df5d9cafb2f4b.png 661w, https:\/\/assets.www.gsbet888.com\/uploads\/2023\/11\/4d640dda86099ae6090df5d9cafb2f4b-300x131.png 300w\" sizes=\"(max-width: 661px) 100vw, 661px\" \/><\/p>\n<p style=\"text-align: justify;\">\u603b\u7ed3\uff0c\u829d\u52a0\u54e5\u5927\u5b66\u7684Viresh H. Rawal\u6559\u6388\u56e2\u961f\u4ee521\u6b65\u9996\u6b21\u5b8c\u6210\u4e86(+)-Heilonine\u7684\u5168\u5408\u6210\u3002\u5176\u4e2d\uff0c\u5173\u952e\u6b65\u9aa4\u4e3b\u8981\u6d89\u53ca: Rh\u50ac\u5316\u7684[2+2+2]\u73af\u5316\u5f02\u6784\u5316(Rh catalyzed [2 + 2 + 2] cycloisomerization reaction); \u4e0d\u5bf9\u79f0Diels\u2013Alder\u53cd\u5e94 (asymmetric Diels\u2013Alder raection ); Robinson\u73af\u5316 (Robinson annulation)\u7b49<\/p>\n<h4 style=\"text-align: justify;\">\u53c2\u8003\u6587\u732e\uff1a<\/h4>\n<ul style=\"text-align: justify;\">\n<li>[1] Q.-W. Jiang, M.-W. Chen, K.-J. Cheng, P.-Z. Yu, X. Wei, Z. Shi, <em>Med. Res. Rev. <\/em><strong>2016<\/strong>, <em>36<\/em>, 119. doi:<a href=\"https:\/\/doi.org\/10.1002\/med.21346\"> 10.1002\/med.21346<\/a>.<\/li>\n<li>[2] H.-J. Li, Y. Jiang, P. Li, <em>Nat. Prod. Rep. <\/em><strong>2006<\/strong>, <em>23<\/em>, 735. doi: <a href=\"https:\/\/pubs.rsc.org\/en\/content\/articlelanding\/2006\/NP\/b609306j\">10.1039\/B609306J<\/a>.<\/li>\n<li>[3] Y. Kitamura, M. Nishizawa, K. Kaneko, M. Shiro, Y.-P. Chen, H.-Y. Hsu, <em>Tetrahedron <\/em><strong>1989<\/strong>, <em>45<\/em>, 7281. doi:<a href=\"https:\/\/doi.org\/10.1016\/S0040-4020(01)89188-2\"> 10.1016\/S0040-4020(01)89188-2<\/a>.<\/li>\n<li>[4] X. Wu, S.-w. Chan, J. Ma, P. Li, P.-c. Shaw, G. Lin, <em>J. Ethnopharmacol. <\/em><strong>2018<\/strong>, <em>210<\/em>, 39. doi:<a href=\"https:\/\/doi.org\/10.1016\/j.jep.2017.08.027\"> 10.1016\/j.jep.2017.08.027<\/a>.<\/li>\n<li>[5] S. Saito, Y. Yamamoto, <em>Chem. Rev. <\/em><strong>2000<\/strong>, <em>100<\/em>, 2901. doi: <a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/cr990281x\">10.1021\/cr990281x.<\/a><\/li>\n<li>[6] S. M\u00fcller, B. Liepold, G. J. Roth, H. J. Bestmann, <em>Synlett <\/em><strong>1996<\/strong>, <em>1996<\/em>, 521. doi: <a href=\"https:\/\/www.thieme-connect.de\/products\/ejournals\/abstract\/10.1055\/s-1996-5474\">10.1055\/s-1996-5474.<\/a><\/li>\n<li>[7] P. Duhamel, G. Dujardin, L. Hennequin, J.-M. Poirier, <em>J. Chem. Soc., Perkin Trans. 1 <\/em><strong>1992<\/strong>, 387. doi: <a href=\"https:\/\/pubs.rsc.org\/en\/content\/articlelanding\/1992\/P1\/p19920000387\">10.1039\/P19920000387<\/a>.<\/li>\n<li>[8] Y. Yamamoto, T. Arakawa, R. Ogawa, K. Itoh, <em>J. Am. Chem. Soc. <\/em><strong>2003<\/strong>, <em>125<\/em>, 12143. doi: <a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/ja0358697\">10.1021\/ja0358697.<\/a><\/li>\n<\/ul>\n<p style=\"text-align: justify;\">\u672c\u6587\u7248\u6743\u5c5e\u4e8e\u00a0Chem-Station\u5316\u5b66\u7a7a\u95f4\uff0c \u6b22\u8fce\u70b9\u51fb\u6309\u94ae\u5206\u4eab\uff0c\u672a\u7ecf\u8bb8\u53ef\uff0c\u8c22\u7edd\u8f6c\u8f7d.<\/p>\n<p style=\"text-align: justify;\">\n","protected":false},"excerpt":{"rendered":"\u4f5c\u8005\uff1a\u77f3\u6cb9\u919a \u5bfc\u8bfb\uff1a \u8fd1\u65e5\uff0c\u829d\u52a0\u54e5\u5927\u5b66\u7684Viresh H. Rawal\u6559\u6388\u56e2\u961f\u5728J. Am. Chem. Soc.\u4e0a\uff0c\u4ee5 \u201cEnantioselective Total Synthesis of (+)-Heilonine\u201d\u4e3a\u9898\uff0c\u4ee521\u6b65\u9996\u6b21\u5b8c\u6210\u4e86(+)-Heilonine\u7684\u5168\u5408\u6210\u3002\u5176\u4e2d\uff0c\u5173\u952e\u6b65\u9aa4\u4e3b\u8981\u6d89\u53ca: Rh\u50ac\u5316\u7684[2+2+2]\u73af\u5316\u5f02\u6784\u5316(Rh catalyzed [2 + 2 + 2] cycloisomerization reaction); \u4e0d\u5bf9\u79f0Diels\u2013Alder\u53cd\u5e94 (asymmetric Diels\u2013Alder reaction ); Robinson\u73af\u5316 (Robinson annulation)\u7b49\u3002 \u201cEnantioselective Total Synthesis of (+)-Heilonine Kyle J. Cassaidy and Viresh H. Rawal* J. Am. Chem. Soc., 2021, 143, 16394\u201316400. doi: 10.1021\/jacs.1c08756\u201d \u6b63\u6587\uff1a \u753e\u4f53\u751f\u7269\u78b1\u56e0\u5176\u72ec\u7279\u7684\u9aa8\u67b6\u548c\u7279\u6b8a\u7684\u751f\u7269\u6d3b\u6027\u5f15\u8d77\u4e86\u4f17\u591a\u79d1\u5b66\u5bb6\u5e7f\u6cdb\u7684\u5173\u6ce8[1]\u3002\u4ece\u767e\u5408\u79d1\u85dc\u82a6\u5c5e\u690d\u7269\u4e2d\u5206\u79bb\u5f97\u5230\u85dc\u82a6(Veratrum)\u751f\u7269\u78b1\u5c31\u662f\u5176\u4e2d\u4e4b\u4e00\u3002\u4ece\u7ed3\u6784\u4e0a\u770b\uff0c\u85dc\u82a6(Veratrum)\u751f\u7269\u78b1\u5177\u6709\u5171\u540c\u7684C-nor-D-homo\u753e\u4f53\u9aa8\u67b6\uff0c\u800c\u6839\u636e\u5176\u4e0e\u54cc\u5576\u73af(F\u73af)\u7684\u8fde\u63a5\u65b9\u5f0f\u53ef\u5206\u4e3a\u4e09\u7c7b\uff1acevanine\u578b\u3001veratramine\u578b\u548cjervine\u578b\uff08Figure 1\uff09[2]\u3002Heilonine (1)\u5c31\u662fcevanine\u578b\u751f\u7269\u78b1\uff0c\u5176\u662f\u7531\u65e5\u672c\u79d1\u5b66\u5bb6Koh Kaneko \u6559\u6388\u53ca\u5176\u540c\u4e8b\u4e8e1989\u5e74\u4ece\u9ed1\u9f99\u6c5f\u7701\u767e\u5408\u79d1\u690d\u7269\u5e73\u8d1d\u6bcdFritillaria Ussuriensis Maxim.\u4e2d\u5206\u79bb\u83b7\u5f97 (Figure 1)[3]\uff0c\u5e76\u4e14\u5176\u88ab\u8ba4\u4e3a\u662f\u91cd\u8981\u7684\u4e2d\u8349\u836f\u201c\u8d1d\u6bcd\u201d\u7684\u6210\u5206(\u4f20\u7edf\u4e2d\u533b\u4e2d\u7528\u6765\u9547\u9759\u3001\u6b62\u54b3\u548c\u795b\u75f0) [4]\u3002\u6b64\u5916\uff0cKoh Kaneko \u6559\u6388\u901a\u8fc7\u901a\u8fc7NMR\u548cX\u5c04\u7ebf\u6676\u4f53\u5b66\u5206\u6790\u9610\u660e\u4e86\u5176\u5177\u6709\u590d\u6742\u516d\u73af\u7ed3\u6784\u548c\u4e5d\u4e2a\u7acb\u4f53\u4e2d\u5fc3\u3002\u8fd1\u65e5\uff0cViresh H. Rawal\u6559\u6388\u56e2\u4ee521\u6b65\u9996\u6b21\u5b8c\u6210\u4e86(+)-Heilonine\u7684\u5168\u5408\u6210\uff0c\u5e76\u53d1\u8868\u4e8eJ. Am. Chem. Soc.\u4e0a\u3002 \u9996\u5148\uff0c(+)-Heilonine (1)\u5177\u6709\u590d\u6742\u7684\u516d\u73af\u7ed3\u6784\u4ee5\u53ca9\u4e2a\u7acb\u4f53\u4e2d\u5fc3\u3002\u57fa\u4e8e\u4e0a\u8ff0\u9aa8\u67b6\uff0c\u4f5c\u8005\u5bf9(+)-Heilonine (1)\u8fdb\u884c\u4e86\u76f8\u5173\u7684\u9006\u5408\u6210\u5206\u6790(Scheme 1)\u3002\u5373\u4ee5\u919bG\u548c\u70ef\u9187\u7845\u919aF\u4e3a\u539f\u6599\u7ecf\u4e0d\u5bf9\u79f0Diels-Alder\u73af\u52a0\u6210\u83b7\u5f97\u516d\u5143\u73afE\uff0cE\u7ecfRobinson\u73af\u5316\u5f97\u5230\u780c\u5757\u53cc\u73af\u4e8c\u7094C\u3002\u53e6\u5916\u4e00\u4e2a\u780c\u5757\u54cc\u5576\u916eD\u53ef\u7531\u4e19\u9170\u5316\u5408\u7269H\u548c\u919b\u7ecf\u4e0d\u5bf9\u79f0Evans aldol\u53cd\u5e94\u4ee5\u53ca lactamization\uff08\u5f15\u5165N\uff09\u5408\u6210\u3002\u53cc\u73af\u4e8c\u7094C\u548c\u54cc\u5576\u916eD\u4e3a\u539f\u6599\u7ecf\u70f7\u57fa\u5316\u53cd\u5e94\u5f97\u4e2d\u95f4\u4f53B\uff0cB\u901a\u8fc7Rh\u50ac\u5316\u7684[2+2+2]\u73af\u5316\u5f02\u6784\u5316\u5408\u6210\u5173\u952e\u780c\u5757A[5]\u3002\u6700\u540e\uff0c\u5173\u952e\u4e2d\u95f4\u4f53A\u901a\u8fc7\u975e\u5bf9\u6620\u9009\u62e9\u6027\u7532\u57fa\u5316\u548c\u6c27\u5316\u53cd\u5e94\u5b8c\u6210(1)\u7684\u5168\u5408\u6210\u3002 \u9996\u5148\uff0c\u8be5\u5c0f\u7ec4\u5408\u6210\u4e86\u780c\u575717\u548c26\uff0c\u5982Scheme 2, 3\u3002 \u8be5\u5c0f\u7ec4\u5b8c\u6210\u4e86Vilmoraconitine (3)\u7684\u5408\u6210\u8def\u7ebf\u8bbe\u8ba1\uff0c\u5982Scheme 4\u3002 \u603b\u7ed3\uff0c\u829d\u52a0\u54e5\u5927\u5b66\u7684Viresh H. Rawal\u6559\u6388\u56e2\u961f\u4ee521\u6b65\u9996\u6b21\u5b8c\u6210\u4e86(+)-Heilonine\u7684\u5168\u5408\u6210\u3002\u5176\u4e2d\uff0c\u5173\u952e\u6b65\u9aa4\u4e3b\u8981\u6d89\u53ca: Rh\u50ac\u5316\u7684[2+2+2]\u73af\u5316\u5f02\u6784\u5316(Rh catalyzed [2 + 2 + 2] cycloisomerization reaction); \u4e0d\u5bf9\u79f0Diels\u2013Alder\u53cd\u5e94 (asymmetric Diels\u2013Alder raection ); Robinson\u73af\u5316 (Robinson annulation)\u7b49 \u53c2\u8003\u6587\u732e\uff1a [1] Q.-W. Jiang, M.-W. Chen, K.-J. Cheng, P.-Z. 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