title: Studies toward the total synthesis of vinigrol. synthesis of the octalin ring.
abstract: [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.
authors.affiliation: Department of Chemistry, University of Ottawa, Canada.
authors.forename: Louis
authors.initials: L
authors.lastname: Morency
authors.forename: Louis
authors.initials: L
authors.lastname: Barriault
mesh_terms: D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D006358:Hot Temperature; D006859:Hydrogen / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D004224:Diterpenes; C055112:vinigrol; D006859:Hydrogen