Exploitation of chemical predisposition in synthesis: An approach to the manzamenones

Saleh Al-Busafi, Jeremy R. Doncaster, Michael G B Drew, Andrew C. Regana, Roger C. Whitehead

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

Full details of the syntheses of manzamenones A, C and F are reported, using an approach modelled on a plausible biogenetic theory. The key step of the approach is a "one-pot" conversion of the antileukemic cyclopentenone, untenone A, to manzamenone A which occurs in reasonable yield and which proceedsvia a reaction sequence of dehydration, Diels-Alder dimerisation and retro-Dieckmann reaction. The synthetic approach has also been applied to the preparation of a number of shorter alkyl chain analogues of the natural products. Using a combination of NMR and X-ray crystallographic data for the shorter alkyl chain analogues of manzamenone A, it is suggested that the relative stereostructures of the majority of the manzamenones should be revised such that the acyl group at the C2 position lies on α-face and that at the C5 position resides on the β-face.

Original languageEnglish
Pages (from-to)476-484
Number of pages9
JournalJournal of the Chemical Society. Perkin Transactions 1
Issue number4
Publication statusPublished - 2002

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Dimerization
Biological Products
Dehydration
Nuclear magnetic resonance
X rays
manzamenone A
untenone A
cyclopentenone

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Exploitation of chemical predisposition in synthesis : An approach to the manzamenones. / Al-Busafi, Saleh; Doncaster, Jeremy R.; Drew, Michael G B; Regana, Andrew C.; Whitehead, Roger C.

In: Journal of the Chemical Society. Perkin Transactions 1, No. 4, 2002, p. 476-484.

Research output: Contribution to journalArticle

Al-Busafi, Saleh ; Doncaster, Jeremy R. ; Drew, Michael G B ; Regana, Andrew C. ; Whitehead, Roger C. / Exploitation of chemical predisposition in synthesis : An approach to the manzamenones. In: Journal of the Chemical Society. Perkin Transactions 1. 2002 ; No. 4. pp. 476-484.
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