Total synthesis of (+/-)-aplykurodinone-1: traceless stereochemical guidance.

Total synthesis of (+/-)-aplykurodinone-1: traceless stereochemical guidance.
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DOI:
10.1021/ja1035495
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发表时间:
2010-07-21
影响因子:
15
通讯作者:
Danishefsky, Samuel J.
Danishefsky, Samuel J.
中科院分区:
化学1区
文献类型:
--
作者:
Zhang, Yandong;Danishefsky, Samuel J.

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已完成了高度降解的甾体天然产物--黑甲素酮-1(1)的全合成。主要特征包括一个烧瓶水解/逆羟醛/碘内酯序列切除C8羟基亚甲基官能团保留立体化学,和立体选择性安装的C13甲基通过氢化与均相催化剂。
The total synthesis of the highly degraded steroidal natural product, aplykurodinone-1 (1), has been accomplished. Key features include a one-flask hydrolysis/retro-aldol/iodolactonization sequence to excise the C8 hydroxymethylene functionality with retention of stereochemistry, and the stereoselective installation of the C13 methyl group through hydrogenation with homogeneous catalyst.
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