Asymmetric synthesis of the tricyclic core of NGF-inducing cyathane diterpenes via a transition-metal-catalyzed [5 + 2] cycloaddition.
[reaction: see text] A concise asymmetric synthesis of the tricyclic core of cyathane diterpenes is described, based on a novel transition-metal-catalyzed intramolecular [5 + 2] cycloaddition of ynone-vinylcyclopropane 10 (assembled from commercially available (S)-(-)-limonene), which proceeds in 90% yield with >95% selectivity. This strategy provides efficient access (14 steps and 13% overall yield) to potential analogues as well as precursors of nerve growth factor (NGF)-inducing diterpenes.
Wender
P A
PA
Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. wenderp@leland.stanford.edu
Bi
F C
FC
Brodney
M A
MA
Gosselin
F
F
D053138:Cyclohexenes; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000077222:Limonene; D020932:Nerve Growth Factor / Q000187:drug effects / Q000378:metabolism; D013729:Terpenes / Q000737:chemistry
D053138:Cyclohexenes; D004224:Diterpenes; D013729:Terpenes; C430643:allocyathin B2; C430644:scabronine E; D020932:Nerve Growth Factor; D000077222:Limonene