Remote 1,5-stereoinduction in boron aldol reactions of methyl ketones: application to the convergent assembly of the 1,3-polyol sequence of (+)-roxaticin

被引：67

作者：

Paterson, I ^{[1
]}

Collett, LA ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 06期

关键词：

roxaticin; boron aldol; macrolide; antifungal; remote stereoinduction;

D O I：

10.1016/S0040-4039(00)02205-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

By exploiting 1,5-anti stereoinduction in the boron aldol coupling of the beta -alkoxy methyl ketones 6 and 8 with aldehydes 7 and 9, the convergent synthesis of 2, corresponding to the fully protected polyol sequence of the 30-membered macrolide, (+)-roxaticin (1), was achieved in an efficient manner (15 steps and 24.0% yield from ketone 15). (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：1187 / 1191

页数：5

共 25 条

[1]

[Anonymous], 1984, MACROLIDE ANTIBIOTIC

[2]

[Anonymous], 1997, ORG REACT

[3] CHIRAL SYNTHESIS VIA ORGANOBORANES .24. B-ALLYLBIS(2-ISOCARANYL)BORANE AS A SUPERIOR REAGENT FOR THE ASYMMETRIC ALLYLBORATION OF ALDEHYDES [J].