Open AccessSix-Step Synthesis of Alcyopterosin A, a Bioactive Illudalane Sesquiterpene with a gem-Dimethylcyclopentane Ring
Author(s) -
Tung T. 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) - cycloisomerization , chemistry , ring (chemistry) , tandem , context (archaeology) , stereochemistry , sesquiterpene , enyne , alkyne , combinatorial chemistry , catalysis , organic chemistry , biology , paleontology , materials science , composite material
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.