The stereocontrolled total synthesis of altohyrtin A/spongistatin 1:: the southern hemisphere EF segment

被引：36

作者：

Paterson, I ^{[1
]}

Coster, MJ ^{[1
]}

Chen, DYK ^{[1
]}

Aceña, JL ^{[1
]}

Bach, J ^{[1
]}

Keown, LE ^{[1
]}

Trieselmann, T ^{[1
]}

机构：

[1] Univ Cambridge, Chem Lab, Cambridge CB2 1EW, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2005年 / 3卷 / 13期

关键词：

D O I：

10.1039/b504149j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The fully functionalised C29-C51 southern hemisphere of altohyrtin A/spongistatin 1 (1), incorporating the E- and F-ring tetrahydropyran rings and the unsaturated side chain, has been synthesised in a highly convergent and stereocontrolled manner. Key steps in the synthesis of this phosphonium salt include four highly diastereoselective, substrate-controlled, boron aldol reactions to establish key C-C bonds and accompanying stereocentres, where the introduction of the chlorodiene side chain and the C47 hydroxyl-bearing centre were realised by exploiting remote stereoinduction from the F-ring tetrahydropyran.

引用

页码：2420 / 2430

页数：11

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