Total synthesis of (-)-denticulatins A and B using efficient methods of acyclic stereocontrol.

被引：68

作者：

Paterson, I

Perkins, MV

机构：

[1] University Chemical Laboratory, Cambridge CB2 1EW, Lensfield Road

[2] Department of Chemistry, Flinders University, Adelaide, SA 5001

来源：

TETRAHEDRON | 1996年 / 52卷 / 05期

关键词：

D O I：

10.1016/0040-4020(95)01015-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of (-)-denticulatin B (2) was achieved in 9 steps (20% yield), with 70% overall diastereoselectivity, starting from the ethyl ketone (R)-9. Most of the stereochemistry was introduced by substrate-based control. Key steps include the boron-mediated aldol/reduction, 9 --> 22, the titanium-mediated aldol coupling,26 + 8 --> 38, and the directed cyclisation, 35 --> 2. Epimerisation at C-10 in 35 led to (-)-denticulatin A (1).

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页码：1811 / 1834

页数：24

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