Synthesis of the non-adjacent bis-THF core of cis-sylvaticin using a double oxidative cyclisation

A short synthesis of the non-adjacent bis-THF core of the Annonaceous acetogenin cis-sylvaticin (1) is described. C(2) Symmetrical (Z,E,E,Z)- and (E,E,E,E)-tetraenes and were synthesised in six and three steps respectively from (1E,5E,9E)-cyclododeca-1,5,9-triene. Subsequent permanganate promoted as...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2009-01, Vol.7 (5), p.1017-1024
Main Authors: Bhunnoo, Riaz A, Hobbs, Heather, Lainé, Dramane I, Light, Mark E, Brown, Richard C D
Format: Article
Language:English
Subjects:
Cyclization
Furans - chemical synthesis
Furans - chemistry
Oxidation-Reduction
Polyenes - chemistry
Stereoisomerism
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Summary:A short synthesis of the non-adjacent bis-THF core of the Annonaceous acetogenin cis-sylvaticin (1) is described. C(2) Symmetrical (Z,E,E,Z)- and (E,E,E,E)-tetraenes and were synthesised in six and three steps respectively from (1E,5E,9E)-cyclododeca-1,5,9-triene. Subsequent permanganate promoted asymmetric bi-directional oxidative cyclisation of tetraene was used to create the non-adjacent bis-THF core of 1, installing seven of the nine stereogenic centres present in the natural product in a single step. Desymmetrization of the oxidative cyclisation product by mono-tosylation gave access to a C11-C32 fragment of cis-sylvaticin.
ISSN:1477-0520
1477-0539
DOI:10.1039/b813201a