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

S Al-Busafi, JR Doncaster, MGB Drew…

Index: Al-Busafi, Saleh; Doncaster, Jeremy R.; Drew, Michael G. B.; Regana, Andrew C.; Whitehead, Roger C. Journal of the Chemical Society. Perkin Transactions 1, 2002 , # 4 p. 476 - 484

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Citation Number: 23

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 proceeds via a reaction sequence of dehydration, Diels–Alder dimerisation and retro-Dieckmann reaction. The synthetic approach has also ...