Diastereoselective synthesis of the tetrahydropyranoid core of the polyketide herbicide herboxidiene and model studies pertaining to attachment of the side-chain

被引：12

作者：

Banwell, MG

Bui, CT

Simpson, GW

机构：

[1] Australian Natl Univ, Res Sch Chem, Inst Adv Studies, Canberra, ACT 0200, Australia

[2] Univ Melbourne, Sch Chem, Parkville, Vic 3052, Australia

[3] CSIRO, Clayton S MDC, Vic 3169, Australia

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 04期

关键词：

D O I：

10.1039/a705907h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A diastereoselective synthesis of compound 2, which embodies the tetrahydropyranyl core of the polyketide herbicide herboxidiene (1), has been developed using asymmetric epoxidation of nerol as the initial step, Ketone 2 has been elaborated to phosphine oxide 24 which engages in a Horner-Wittig reaction with nonanal to give the E,E-diene 27, an analogue of herboxidiene, However, unlike compound 1, congeners 2 and 27 are not phytotoxic.

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页码：791 / 799

页数：9

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