Intramolecular Alkynylogous Mukaiyama Aldol Reaction Starting from Bicyclic Alkanones Tethered to Alkynyl Esters: Formal Total Synthesis of (±)-Hamigeran B

被引：43

作者：

Miesch, Laurence ^{[1
]}

Welsch, Tania ^{[1
]}

Rietsch, Vincent ^{[1
]}

Miesch, Michel ^{[1
]}

机构：

[1] Univ Strasbourg, Inst Chim, CNRS, ULP,UMR 7177, F-67008 Strasbourg, France

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2009年 / 15卷 / 17期

关键词：

aldol reaction; allenes; cascade reactions; stereoselectivity; total synthesis; CASCADE REACTIONS; ASYMMETRIC-SYNTHESIS; SILYL GROUPS; HAMIGERAN-B; CONSTRUCTION; ALLENOATES; KETONES; BOND;

D O I：

10.1002/chem.200802309

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

tert-Butyldimethylsilyltriflate (TBSOTf)/NEt3 treatment of alkynyl esters tethered to bicycloalkanones led to tricyclic allenoates with total diastereoselectivity for the ring junction. The allenoates result from an intramolecular alkynylogous Mukaiyama aldol reaction promoted by a TBSOTf/NEt3 dual activation, with key intermediates of silylalkynylketene acetals. This novel methodology was illustrated by a formal total synthesis of (+/-)-hamigeran B

引用

页码：4394 / 4401

页数：8

共 33 条

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