阿普拉毒素A的恶唑啉类似物的合成

Synthesis of an oxazoline analogue of apratoxin A.

作者信息

Zou Bin, Wei Jingjun, Cai Guorong, Ma Dawei

机构信息

State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.

出版信息

Org Lett. 2003 Sep 18;5(19):3503-6. doi: 10.1021/ol035332y.

DOI:10.1021/ol035332y

PMID:12967310

Abstract

[structure: see text] Michael addition of Me(2)Cu(CN)Li(2) to alpha,beta-unsaturated lactone 7 derived from beta-hydroxyl ketone 5 provides lactone 8, which is converted to alcohol 11 using Oppolzer's methodology as the key step. Connection of 11 with the l-proline moiety and subsequent installation of an oxazoline ring affords 16, which is coupled with tripeptide 21; subsequent macrocyclization then furnishes 4, an oxazoline analogue of apratoxin A.

摘要

[结构：见正文] 将二甲基铜锂（Me(2)Cu(CN)Li(2)）与由β-羟基酮5衍生而来的α,β-不饱和内酯7进行迈克尔加成反应，得到内酯8，以内酯8为关键步骤，采用奥波泽尔方法将其转化为醇11。将11与L-脯氨酸部分连接，随后安装恶唑啉环，得到16，将其与三肽21偶联；随后进行大环化反应，得到4，即阿普拉毒素A的恶唑啉类似物。