Total synthesis of (+)-crocacin C
Total synthesis of (+)-crocacin C
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DOI：
10.1016/s0040-4020(01)00940-1
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发表时间：
2001-11-12
期刊：
影响因子：
2.1
通讯作者：
Laxman, P
中科院分区：
文献类型：
--
作者：
Chakraborty, TK;Jayaprakash, S;Laxman, P
全合成强效抗真菌药。和细胞毒剂(+)-藏红花C在光学纯形式以下收敛策略的详细描述。该合成还建立了具有（6S,7S,8R,9S）构型的分子的绝对立体化学。以2-恶唑烷硫酮为手性辅助物，通过Ti（IV）介导的非对映选择性“非evans”醛醇反应建立了C8和C9立体中心，而通过Sharpless环氧化法制备的C6-C7手性环氧化合物的二甲基铜酸锂开孔建立了剩余的两个立体中心。2001爱思唯尔科学有限公司版权所有。
The total synthesis of potent antifungal. and cytotoxic agent (+)-crocacin C in optically pure form following a convergent strategy is described here in detail. The synthesis also established the absolute stereochemistry of the molecule having a (6S,7S,8R,9S) configuration. While C8 and C9 stereocenters were built following a Ti(IV)-mediated diastereoselective 'non-Evans' aldol reaction based on 2-oxazolidinethione chiral auxiliary, lithium dimethylcuprate opening of a C6-C7 chiral epoxide prepared by Sharpless epoxidation method established the remaining two stereocentres. (C) 2001 Elsevier Science Ltd. All rights reserved.