Efficient asymmetric syntheses of (+)-strictifolione

被引：46

作者：

Enders, D

Lenzen, A

Müller, M

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany

[2] Forschungszentrum, Inst Biotechnol 2, D-52425 Julich, Germany

来源：

SYNTHESIS-STUTTGART | 2004年 / 09期

关键词：

asymmetric synthesis; enzymatic reduction; hydrazones; natural products; organocatalysis;

D O I：

10.1055/s-2004-822387

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric synthesis and a formal asymmetric synthesis of (+)-strictifolione are described. As key step in both approaches the Julia-Kocienski olefination to create an E-configured alkene was used. The anti-1,3-diol moiety was synthesized by employing a SAMP-hydrazone alpha,alpha'-bisalkylation/deoxygenation protocol and the stereocentre of the lactone unit is based on an enzymatic reduction with baker's yeast. Alternatively, a lactone precursor could be efficiently synthesized by a (S)-proline catalyzed alpha-oxyamination of pent-4-enal.

引用

页码：1486 / 1496

页数：11

共 47 条

[1]

Blakemore PR, 1998, SYNLETT, P26

[2] Direct catalytic enantioselective α-aminoxylation of ketones:: A stereoselective synthesis of α-hydroxy and α,α′-dihydroxy ketones [J].