Synthetic efforts towards the protoilludenes. A formal synthesis of Delta(7)-protoilludene

An improved route to 5,8,8-trimethylbicyclo[4.3.0]-4-nonen-3-one, a key intermediate for the synthesis of the protoilludane skeleton and in particular Delta(7)-protoilludene, is reported. Attempts on an alternative synthesis of Delta(6)-protoilludene based on a phenylsulfonyl allene cycloaddition re...

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Bibliographic Details
Published inTetrahedron Vol. 59; no. 19; pp. 3461 - 3466
Main Authors Hansen, TV, Skattebol, L, Stenstrom, Y
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 05.05.2003
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
allene
SESQUITERPENE ARYL ESTERS
METABOLITES
cycloaddition
ABSOLUTE-CONFIGURATION
GENERATION
ARMILLARIA-MELLEA
protoilludene
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Summary:An improved route to 5,8,8-trimethylbicyclo[4.3.0]-4-nonen-3-one, a key intermediate for the synthesis of the protoilludane skeleton and in particular Delta(7)-protoilludene, is reported. Attempts on an alternative synthesis of Delta(6)-protoilludene based on a phenylsulfonyl allene cycloaddition reaction is also presented. (C) 2003 Elsevier Science Ltd. All rights reserved.
ISSN:0040-4020
DOI:10.1016/S0040-4020(03)00480-0