Six-Step Synthesis of Alcyopterosin A, a Bioactive Illudalane Sesquiterpene with a gem-Dimethylcyclopentane Ring

Strategic pairing of ring openings and cyclo-isomerization provides rapid and efficient "open and shut" entry into sparsely functionalized illudalanes, as exemplified here in the context of a six-step synthesis of alcyopterosin A. Key steps include a tandem ring-opening fragmentation/olefi...

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Bibliographic Details
Published inOrganic letters Vol. 18; no. 14; pp. 3470 - 3473
Main Authors Hoang, Tung T., Birepinte, Melodie, Kramer, Nicholas M., Dudley, Gregory B.
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 15.07.2016
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
TRIFLATE
CATALYSIS
OLEFINATION
TANDEM NUCLEOPHILIC ADDITION/FRAGMENTATION
METALATIVE REPPE REACTION
CYCLOISOMERIZATION
CONDENSATION
CYCLOPROPYLMETHANOLS
1,N-ENYNES
ENYNES
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Summary:Strategic pairing of ring openings and cyclo-isomerization provides rapid and efficient "open and shut" entry into sparsely functionalized illudalanes, as exemplified here in the context of a six-step synthesis of alcyopterosin A. Key steps include a tandem ring-opening fragmentation/olefination process for preparing a neopentyl-tethered 1,6-enyne, ring-opening olefination telescoped with alkyne homologation, and Rh-catalyzed oxidative cycloisomerization.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b01665