Total synthesis of herboxidiene, a complex polyketide from Streptomyces species A7847

Banwell, Martin; McLeod, Malcolm; Premraj, Rajaratnam; Simpson, Gregory Wayne

Total synthesis of herboxidiene, a complex polyketide from Streptomyces species A7847

Date

2000

Authors

Banwell, Martin

McLeod, Malcolm

Premraj, Rajaratnam

Simpson, Gregory Wayne

Publisher

International Union of Pure and Applied Chemistry

Abstract

A formal total synthesis of the polyketide herboxidiene (1) has been achieved by Homer-Wittig coupling of the side-chain fragment 12-epi-(2) with the tetrahydropyran-2-acetic acid derivative (3) followed by desilylation of the resulting triene (19) and hydroxyl-directed mono-epoxidation of the ensuing bis-homoallylic alcohol (20).

Keywords

Keywords: acetic acid derivative; allyl alcohol; herboxidiene; hydroxyl group; polyketide; tetrahydropyran derivative; unclassified drug; chemical reaction; conference paper; epoxidation; nonhuman; priority journal; reaction analysis; Streptomyces; synthesis

URI

http://hdl.handle.net/1885/90553

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ANU Research Publications

Source

Pure and Applied Chemistry

Type

Journal article

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Total synthesis of herboxidiene, a complex polyketide from Streptomyces species A7847

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