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