Diastereoselective hydroformylation of acyclic olefins:: Efficient construction of an all-anti stereotriade building block for polyketide synthesis

被引：26

作者：

Breit, B ^{[1
]}

Zahn, SK ^{[1
]}

机构：

[1] Univ Marburg, Fachbereich Chem, D-35043 Marburg, Germany

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 14期

关键词：

D O I：

10.1016/S0040-4039(98)00158-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The hydroformylation of 2-phenyl-4-(prop-2-enyl)[1,3]dioxanes has been studied. anti-Acetals 1a,b were found to give extraordinarily high diastereoselectivity on hydroformylation, giving rise to the formation of the all-anti stereotriades 2a,b. The origin of this stereoselectivity may be related to the preferred conformation of the actetals 3 in solution, as determined by 2D-NOESY NMR experiments and force field calculations (MM3). Hydroformylation of la afforded an intermediate for a short and efficient synthesis of a key building block for the total synthesis of the macrolide antibiotic bafilomycin A(1). (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：1901 / 1904

页数：4

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