An approach to the total synthesis of lankacidins: synthesis of the requisite building blocks

被引：31

作者：

Brain, CT ^{[1
]}

Chen, A ^{[1
]}

Nelson, A ^{[1
]}

Tanikkul, N ^{[1
]}

Thomas, EJ ^{[1
]}

机构：

[1] Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 07期

基金：

英国工程与自然科学研究理事会;

关键词：

lankacidin; azetidinone; Mitsunobu reaction;

D O I：

10.1016/S0040-4039(00)02260-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A strategy for a total synthesis of lankacidin C 1 is outlined and the requisite building blocks synthesised. The azetidinone 4 was prepared from methyl but-2-ynoate 6 via a route which features the stereoselective addition of a tributyltin cuprate to the alkyne, an asymmetric aldol condensation and formation of the azetidinone by an intramolecular Mitsunobu reaction. The aldehyde 3 was prepared From dimethyl malate 18 and the sulfone 3 from prop-2-ynol 27 again using asymmetric aldol reactions as key steps. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：1247 / 1250

页数：4

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