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

Martin Banwell; Malcolm McLeod; Rajaratnam Premraj; Gregory Simpson

doi:10.1351/pac200072091631

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

Martin Banwell^*
, Malcolm McLeod
, Rajaratnam Premraj
, Gregory Simpson

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

24 Citations (Scopus)

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).

Original language	English
Pages (from-to)	1631-1634
Number of pages	4
Journal	Pure and Applied Chemistry
Volume	72
Issue number	9
DOIs	https://doi.org/10.1351/pac200072091631
Publication status	Published - 2000

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

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).",

author = "Martin Banwell and Malcolm McLeod and Rajaratnam Premraj and Gregory Simpson",

year = "2000",

doi = "10.1351/pac200072091631",

language = "English",

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T1 - Total synthesis of herboxidiene, a complex polyketide from Streptomyces species A7847

AU - Banwell, Martin

AU - McLeod, Malcolm

AU - Premraj, Rajaratnam

AU - Simpson, Gregory

PY - 2000

Y1 - 2000

N2 - 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).

AB - 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).

UR - https://www.scopus.com/pages/publications/0034583411

U2 - 10.1351/pac200072091631

DO - 10.1351/pac200072091631

M3 - Article

SN - 0033-4545

VL - 72

SP - 1631

EP - 1634

JO - Pure and Applied Chemistry

JF - Pure and Applied Chemistry

IS - 9

ER -

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

Abstract

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