{"id":13656,"date":"2017-04-05T11:01:49","date_gmt":"2017-04-05T03:01:49","guid":{"rendered":"\/\/www.gsbet888.com\/?p=13656"},"modified":"2019-08-02T18:53:22","modified_gmt":"2019-08-02T10:53:22","slug":"communesin-f%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\/2017\/04\/communesin-f%e5%85%a8%e5%90%88%e6%88%90.html","title":{"rendered":"(-)-Communesin F\u5168\u5408\u6210"},"content":{"rendered":"
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\u6295\u7a3f\u4f5c\u8005 \u9648\u5143\u91d1<\/strong><\/p>\n

\u5432\u54da\u751f\u7269\u78b1 Communesin \u5bb6\u65cf\u662f 8 \u4e2a\u5177\u6709\u590d\u6742\u4e03\u73af\u7cfb\u7684\u5929\u7136\u4ea7\u7269\u3002\u56e0\u5177\u6709\u72ec\u7279\u7684\u5316\u5b66\u7ed3 \u6784(4 \u4e2a\u6c2e\u539f\u5b50\u6784\u6210\u7f55\u89c1\u7684\u4e0a\u4e0b\u4e24\u4e2a aminal \u7f29\u919b\u80fa\u57fa\u56e2\uff0c\u5916\u52a0\u4e24\u4e2a\u8fde\u7eed\u624b\u6027\u5b63\u78b3)\u548c\u6709\u8da3\u7684\u751f\u7269\u6d3b \u6027\u800c\u6210\u4e3a\u660e\u661f\u5206\u5b50\uff0c\u5c24\u5176\u662f Communesin F \u7684\u5168\u5408\u6210\u5907\u53d7\u5316\u5b66\u5bb6\u9752\u7750\u3002\u5b8c\u6210 Communesin \u8fd9 \u6837\u9ad8\u96be\u5ea6\u7684\u5206\u5b50\u9700\u8981\u8bbe\u8ba1\u5de7\u5999\u3001\u65b0\u9896\u7684\u5408\u6210\u7b56\u7565\u3002\u57fa\u4e8e\u5bf9\u73b0\u6709 5 \u6761\u5168\u5408\u6210\u8def\u7ebf\u7684\u5206\u6790\uff0c\u6768\u7389 \u8363\u7b49\u4eba\u53d1\u73b0\u76ee\u524d\u5c1a\u672a\u6709\u6548\u89e3\u51b3\u4e24\u4e2a\u5173\u952e\u95ee\u9898:(1)Communesin F \u7684\u50ac\u5316\u4e0d\u5bf9\u79f0\u7684\u5168\u5408\u6210;(2) \u4e0b\u65b9 aminal \u57fa\u56e2\u7684\u56db\u73af\u4f53\u7cfb\u4e00\u6b65\u4eff\u751f\u6784\u5efa\u3002\u4e3a\u6b64\uff0c\u7814\u7a76\u4eba\u5458\u521b\u65b0\u6027\u8bbe\u8ba1\u51fa Ir \u50ac\u5316\u65b0\u7b56\u7565\uff0c \u5b9e\u73b0\u4e86 3-\u53d6\u4ee3\u5432\u54da\u548c\u82ef\u80fa\u884d\u751f\u7684\u70ef\u4e19\u57fa\u4eb2\u7535\u8bd5\u5242\uff0c\u5206\u5b50\u95f4\u7684\u4e00\u6b65\u4eff\u751f\u73af\u5316\uff0c\u9ad8\u6548\u6784\u5efa CDEF \u56db\u73af\u3002\u8be5\u4e32\u8054\u53cd\u5e94\u5177\u6709\u9ad8\u5ea6\u9009\u62e9\u6027(\u5bf9\u6620\u4f53\u3001\u975e\u5bf9\u6620\u4f53\uff0c\u533a\u57df)\u548c\u7ecf\u6d4e\u6027(\u6b65\u9aa4\u3001\u539f\u5b50\u3001\u6c27 \u5316\u8fd8\u539f)\u7684\u4f18\u70b9\u3002\u5728\u5168\u5408\u6210\u6700\u540e\u9636\u6bb5\uff0c\u5229\u7528\u626d\u66f2\u9170\u80fa LAH \u8fd8\u539f\u4e3a O, N-hemiaminal\uff0c\u7532\u78fa\u9170 \u5316\u4f34\u968f\u4e9a\u80fa\u79bb\u5b50\u7684\u73af\u5316\u53cd\u5e94\u5f97\u5230\u590d\u6742\u4e03\u73af\u9aa8\u67b6\uff0c\u8131 Boc\uff0c\u7b80\u6d01\u5b8c\u6210\u4e86(-)-communesin F \u7684\u50ac \u5316\u4e0d\u5bf9\u79f0\u5168\u5408\u6210\u3002 [1]\u8fd9\u4e00\u5de5\u4f5c\u5341\u5206\u6f02\u4eae\uff0c\u6700\u4e3a\u7a81\u51fa\u7684\u662f Tetracyclic Aminal \u7684\u6784\u7b51\u548c\u6700\u540e\u4e00\u6b65 \u7684\u8fd8\u539f\u5173\u73af\u53cd\u5e94\u3002\u4e0b\u9762\u5c31\u8fd9\u4e00\u5de5\u4f5c\u8fdb\u884c\u8be6\u7ec6\u89e3\u8bfb\u3002<\/p>\n

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Ir-Catalyzed Asymmetric Total Synthesis of (\u2212)-Communesin F<\/p>\n

Xiao Liang, Tian-Yuan Zhang, Xue-Yi Zeng, Yu Zheng, Kun Wei, and Yu-Rong Yang.<\/p>\n

J. Am. Chem. Soc.<\/em>2017<\/strong>, 139<\/em>, 3364\u22123367.\u00a0DOI: 10.1021\/jacs.7b00854<\/a><\/p><\/blockquote>\n

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\u9996\u5148\u4f5c\u8005\u5bf9\u56db\u73af\u4f53\u7cfb\u6784\u7b51\u7684\u65b9\u6cd5\u5b66\u8fdb\u884c\u7814\u7a76\u3002\u4f5c\u8005\u6839\u636e\u4e4b\u524d\u81ea\u5df1\u8bfe\u9898\u7ec4\u7684\u5de5\u4f5c\uff0c\u8bd5\u56fe\u7528 \u94f1\u50ac\u5316\u4e0d\u5bf9\u79f0\u73af\u5316\u7684\u65b9\u6cd5\u8fdb\u884c\u6784\u7b51\u3002\u5982 scheme 1.<\/p>\n

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\u00a0 \u00a0 \u4e8e\u662f\uff0c\u4f5c\u8005\u7528\u4e4b\u524d\u5df2\u62a5\u9053\u8fc7\u7684\u6761\u4ef6\uff0c\u5bf9 17\uff0c18 \u8fdb\u884c\u7684\u53cd\u5e94\u8fdb\u884c\u7814\u7a76\u3002\u9057\u61be\u7684\u662f\uff0c\u5e76\u672a\u5f97\u5230\u76ee\u6807\u5316\u5408\u7269 20\uff0c\u800c\u662f\u5f97\u5230\u4e86\u5316\u5408\u7269 19.\u4f5c\u8005\u53d7 Trost \u5408\u6210(\u2212)-perophoramidine \u5de5\u4f5c\u7684\u542f\u53d1 [2]\uff0c\u5728\u5432\u54da\u73af 4 \u4f4d\u5f15\u5165\u4e86\u6eb4\u539f\u5b50\uff0c\u628a 3 \u4f4d\u7684\u7532\u57fa\u6539\u4e3a TBS \u53d6\u4ee3\u7684\u4e59\u6c27\u57fa\uff0c\u7528 carreira \u914d\u4f53 L1 \u8fdb\u884c\u53cd\u5e94\uff0c\u53d6\u5f97\u4e86\u826f\u597d\u7684\u6548\u679c\u3002<\/p>\n

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\u6839\u636e Table1 \u53ef\u77e5\uff0cPd \u50ac\u5316\u5242\u50ac\u5316\u65f6\u4e3b\u8981\u4ee5 21 \u4e3a\u4e3b\uff0c\u94f1\u50ac\u5316\u5242\u50ac\u5316\u65f6\u624d\u80fd\u5b9e\u73b0\u4e3b\u8981 \u4ee5 14a \u4e3a\u4e3b\u3002\u5982\u679c\u6309\u7ecf\u5178\u7684 Tsuji-Trost Reaction \u673a\u7406\uff0c\u5432\u54da\u73af\u5e94\u4ee5 3 \u4f4d\u8fdb\u884c\u53cd\u5e94\uff0c\u56e0\u4e3a\u8fd9\u624d \u662f\u4e00\u4e2a\u597d\u7684 nucleophile\u3002\u4e8b\u5b9e\u4e0a\uff0c21 \u7684\u751f\u6210\u6b63\u53cd\u6620\u8fd9\u4e2a\u4e8b\u5b9e\u3002\u5f53\u4f7f\u7528\u94f1\u50ac\u5316\u5242\u65f6\uff0c\u5219\u4e0d\u540c \u4e8e\u8fd9\u79cd\u60c5\u51b5\uff0c\u5982 s\u2019cheme2 \u3002\u5373\u4f7f\u5e76\u672a\u5f97\u5230\u76ee\u6807\u5316\u5408\u7269 20\uff0c\u4f46\u662f\u8fd9\u4e00\u4e8b\u5b9e\u5374\u53cd\u6620\u4e86\u94f1\u50ac\u5316\u4e0b \u53cd\u5e94\u4e0d\u540c\u4e8e Tsuji-Trost Reaction\uff0c\u6216\u8005\u8bf4\u4e0d\u6ee1\u8db3\u4e8e\u7ecf\u5178\u7684 Tsuji-Trost Reaction \u673a\u7406\u3002\u6211\u6b64\u5904\u8ba8 \u8bba\u7684\u76ee\u7684\u5b9e\u9645\u4e0a\u662f\u60f3\u8bf4:scheme 1 \u6240\u53cd\u6620\u7684\u673a\u7406\u662f\u7b26\u5408\u7ecf\u5178\u7684 Tsuji-Trost Reaction \u673a\u7406\u7684\uff0c \u6587\u4e2d\u8fd9\u4e00\u8fc7\u7a0b\u662f\u6709\u522b\u4e8e\u7ecf\u5178\u7684 Tsuji-Trost Reaction \u673a\u7406\u7684\u3002\u7528\u8fd9\u4e2a\u56fe\u63cf\u8ff0\u8fd9\u4e00\u8fc7\u7a0b\u662f\u5426\u5408\u9002? \u6211\u4eec\u5982\u4f55\u8003\u8651\u8fd9\u4e00\u8fc7\u7a0b\u5462?<\/p>\n

\u5c06 16N \u4e0a\u7684-COOMe \u4e3a Boc \u540e\uff0cundesired \u4ea7\u7269 21 \u589e\u591a\uff0c\u8bf4\u660e N \u4e0a\u53d6\u4ee3\u57fa\u7684\u7a7a\u963b\u5bf9\u53cd\u5e94\u7684\u533a\u57df\u9009\u62e9\u6027\u6709\u8f83\u5927\u5f71\u54cd\u3002\u5f97\u5230\u76ee\u6807\u5316\u5408\u7269 14a \u540e\uff0c\u5f00\u59cb\u5168\u5408\u6210\u3002<\/p>\n

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\u9996\u5148\uff0c\u4f7f\u7528\u4f7f\u7528\u53d4\u4e01\u9187\u94be\u62d4\u53bb\u5432\u54da\u73af N \u4e0a\u7684 H\uff0c\u7528\u7898\u7532\u70f7\u8fdb\u884c\u7532\u57fa\u5316\u3002\u518d\u7528 CSA \u8131\u53bb TBS \u4fdd\u62a4\u57fa\u3002\u66b4\u9732\u51fa\u9187\u7f9f\u57fa\u540e\u91c7\u7528 Mitsunobu \u53cd\u5e94\u5c06\u7f9f\u57fa\u8f6c\u5316\u4e3a\u4e86 N \u53d6\u4ee3\u57fa\u3002\u968f\u540e\uff0c\u5229\u7528 Lemieux\u2212Johnson oxidation \u628a\u53cc\u952e\u5148\u8f6c\u5316\u4e3a\u919b\u53c8\u5c06\u919b\u8fdb\u884c Pinnick oxidation \u3002\u8fd9\u662f\u4e00\u4e2a\u5c06\u53cc \u952e\u8f6c\u5316\u4e3a\u7fa7\u9178\u7684\u597d\u65b9\u6cd5\uff0c\u5728\u5f88\u591a\u5408\u6210\u4e2d\u90fd\u8fdb\u884c\u4e86\u4f7f\u7528\u3002\u4ea7\u751f\u7684\u7fa7\u9178\u5219\u7528\u91cd\u53e0\u7532\u70f7\u8fdb\u884c\u70f7\u57fa\u5316\u3002 \u4e0b\u4e00\u6b65\u5219\u4e3a\u540e\u7eed\u53cd\u5e94\u57cb\u4e0b\u4e86\u4f0f\u7b14\u3002\u7ecf\u5178\u7684 Gabriel synthesis \u4f7f\u7528\u7684\u662f\u5f3a\u78b1\uff0c\u8fd9\u5e76\u4e0d\u662f\u4e00\u4e2a\u597d \u7684\u6761\u4ef6\uff0c\u56e0\u4e3a\u5f88\u591a\u5e95\u7269\u518d\u6b64\u6761\u4ef6\u4e0b\u4e0d\u517c\u5bb9\u3002\u6240\u4ee5\u8fd9\u91cc\u91c7\u7528\u7684\u662f Ing-Manske procedure\u3002Phth \u6389\u4e0b\u540e\u53d1\u751f\u7684\u662f\u4e00\u4e2a\u81ea\u53d1\u7684\u5185\u9170\u80fa\u5316\u53cd\u5e94\u3002\u8fd9\u91cc\u8003\u8651\u4e3a\u4ec0\u4e48\u4f1a\u81ea\u53d1?\u9170\u80fa\u5316\u540e\u518d\u6b21\u7528 Boc \u4fdd\u62a4\u3002\u5bf9\u5185\u9170\u80fa\u8fdb\u884c\u70f7\u57fa\u5316\uff0c\u5f97\u5230\u7684\u662f\u4e24\u4e2a\u5f02\u6784\u4f53\uff0c\u4f46\u65e0\u9700\u5206\u79bb\uff0c\u7528\u53d4\u4e01\u9187\u94be\u8131\u6389 Boc \u540e\uff0c \u4e00\u52a0\u70ed\uff0cO-\u70f7\u57fa\u5316\u4ea7\u7269\u5f88\u5bb9\u6613\u5c31[3+3]\u8f6c\u5316\u4e3a C \u70f7\u57fa\u5316\u4ea7\u7269\u3002\u8fd9\u91cc\u6709\u4e24\u4e2a\u95ee\u9898\u3002\u4e00\u662f\u4e3a\u4f55\u8fde \u7eed\u7684\u4e24\u6b65\u5148\u4e0a Boc\uff0c\u8ba9\u540e\u518d\u628a\u5b83\u8131\u4e0b\u6765?\u4e8c\u662f[3+3]\u4e3a\u4f55\u5bb9\u6613\u53d1\u751f?\u7b2c\u4e00\u4e2a\u95ee\u9898\uff0cBoc \u662f\u5426\u662f<\/p>\n<\/div>\n<\/div>\n<\/div>\n

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\u6ca1\u5fc5\u8981\u4e0a\u53bb?\u5176\u5b9e\u662f\u5f88\u6709\u5fc5\u8981\u7684\u3002\u56e0\u4e3a Phth \u6389\u4e0b\u4e4b\u540e\uff0c\u5185\u9170\u80fa\u5316\u662f\u4e00\u4e2a\u5e73\u8861\u53cd\u5e94\uff0c\u4e00\u4e2a\u5e73 \u8861\u53cd\u5e94\u662f\u9700\u8981\u6709\u63a8\u52a8\u529b\u624d\u80fd\u53d1\u6325\u5176\u4f5c\u7528\uff0c\u800c\u8fd9\u91cc\u7f3a\u5c11\u7684\u5c31\u662f\u63a8\u52a8\u529b\u3002Boc \u662f\u63a8\u52a8\u529b\u5417?\u53ef\u4ee5 \u8fd9\u6837\u7406\u89e3\uff0c\u4f46\u4e0d\u51c6\u786e\u3002\u5f62\u6210\u9170\u80fa\u540e\uff0c\u9170\u80fa\u5f88\u5bb9\u6613\u7ecf\u8fc7\u4e00\u4e2a\u5e73\u8861\u8fc7\u7a0b\u53c8\u56de\u53bb\u4e86\uff0c\u800c Boc \u4e0a\u53bb\u4e4b \u540e\uff0c\u9170\u80fa\u5728\u53cd\u5e94\u56de\u53bb\u7684\u8fc7\u7a0b\u5c31\u88ab\u6253\u7834\u4e86\uff0c\u5176\u7ed3\u679c\u5c31\u662f\u63a8\u52a8\u4e86\u53cd\u5e94\u7684\u8fdb\u884c\u3002\u7b2c\u4e8c\u4e2a\u95ee\u9898 Boc \u4e0b\u6765\u4e4b\u540e\u5b9e\u9645\u4e0a\u662f\u76f8\u5f53\u4f7f\u9170\u80fa\u7684\u6d3b\u6027\u53c8\u89e3\u653e\u51fa\u6765\uff0c\u540c\u65f6\u5728\u5f3a\u78b1\u4e0b\uff0cN \u4e0a\u7684 H \u53c8\u4f1a\u88ab\u62d4\u51fa\uff0c\u662f [3+3]\u7ed3\u6784\u5bcc\u7535\u5b50\u8bdd\uff0c\u8fd9\u5b9e\u9645\u76f8\u5f53\u4e8e\u6d3b\u5316\u4e86[3+3]\u53cd\u5e94\u4f53\u7cfb\u3002\u8fd9\u4e00\u7406\u5ff5\u5176\u5b9e\u5728\u51e0\u4e2a claisen \u53cd\u5e94 \u4e2d\u4f53\u73b0\u7684\u6dcb\u6f13\u5c3d\u81f4\uff0c\u5982 Eschenmoser-claisen\uff0cIreland-claisen\uff0cJohnosen-claisen\u3002\u5185\u9170\u80fa\u5f62\u6210 \u540e\u518d\u4e00\u6b21 Lemieux\u2212Johnson oxidation\u3002\u968f\u540e Mitsunobu\uff0cHeck\uff0cSN\u20192\uff0c \u5f97\u5230 33 \u540e\uff0c\u79bb Communesin F \u4ec5\u6709\u4e00\u6b65\uff0c\u7136\u800c\u7ecf\u8fc7\u5c1d\u8bd5\uff0c33 \u96be\u4ee5\u8f6c\u5316\u4e3a Communesin F\u3002\u4e3a\u4e86\u907f\u514d\u7ecf\u8fc7 33\uff0c \u4f5c\u8005\u6539\u53d8\u7b56\u7565\uff0c\u7ecf 35 \u5408\u6210 Communesin F\u3002<\/p>\n

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\u53c2\u8003\u6587\u732e\u53ca\u94fe\u63a5<\/h4>\n
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\n[1]\u6768\u7389\u8363\u7814\u7a76\u7ec4\u5728\u5432\u54da\u751f\u7269\u78b1Communesin\u5bb6\u65cf\u7684\u50ac\u5316\u4e0d\u5bf9\u79f0\u5168\u5408\u6210\u7814\u7a76\u4e0a\u53d6\u5f97\u91cd\u8981\u8fdb\u5c55<\/a><\/p>\n[2] Trost, B. M.; Osipov, M.; Kr\u00fcger, S.; Zhang, Y. Chem. Sci. 2015, 6,349.<\/p>\n[3] Ming Yang, Jian Li, and Ang Li, Nature Communications 2015, 6, 6445<\/p>\n

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