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

Tung Thanh Hoang | Zendy; Mélodie Birepinte | Zendy; Nicholas J. Kramer | Zendy; Gregory B. Dudley | Zendy

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

Author(s) -

Tung Thanh Hoang,

Mélodie Birepinte,

Nicholas J. Kramer,

Gregory B. Dudley

Publication year - 2016

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.6b01665

Subject(s) - chemistry , sesquiterpene , ring (chemistry) , stereochemistry , combinatorial chemistry , organic chemistry

Strategic pairing of ring openings and cycloisomerization 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.

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