Studies toward the total synthesis of vinigrol. synthesis of the octalin ring.
[reaction: see text] Herein, we disclose our results regarding various strategies toward the assembly of the octanyl ring of vinigrol. Attempts to generate the problematic eight-membered ring through a ring expansion or via unification of the terminal olefins using the ring-closing metathesis were not successful. The cyclooctane ring was created via a sequential hydroxy Diels-Alder/Claisen rearrangement reaction of diene 55 and N-benzylmaleimide.
Morency
Louis
L
Department of Chemistry, University of Ottawa, Canada.
Barriault
Louis
L
D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D006358:Hot Temperature; D006859:Hydrogen / Q000737:chemistry; D015394:Molecular Structure
D004224:Diterpenes; C055112:vinigrol; D006859:Hydrogen