Synthesis of Natural Oxygenated Monocarbocyclic Sesquiterpenoids from 6,7-Epoxygeranyl Acetate

Natural sesquiterpenes 5-(2′,5′-epoxy-2′,6′,6′-trimethyl)cyclohexyl-3-methyl-1-penten-3-ol ( 5), cis-3-[( E)-5′-hydroxy-3′-methyl-3′-pentenyl]-2,2-dimethyl-4-methylenecyclohexanol (elegansidiol) ( 6), 4-(5′-acetoxy-2′,6′,6′-trimethyl)cyclohex-2′-enyl-3-methyl-1-penten-3-ol ( 7) and 5-acetoxy-3-(3-hy...

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Bibliographic Details
Published in:Tetrahedron 2000-08, Vol.56 (33), p.6099-6113
Main Authors: Barrero, Alejandro F, Alvarez-Manzaneda, Enrique J, Chahboun, Rachid, Rodriguez Rivas, A, Linares Palomino, P
Format: Article
Language:English
Subjects:
cyclization
terpenes
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Summary:Natural sesquiterpenes 5-(2′,5′-epoxy-2′,6′,6′-trimethyl)cyclohexyl-3-methyl-1-penten-3-ol ( 5), cis-3-[( E)-5′-hydroxy-3′-methyl-3′-pentenyl]-2,2-dimethyl-4-methylenecyclohexanol (elegansidiol) ( 6), 4-(5′-acetoxy-2′,6′,6′-trimethyl)cyclohex-2′-enyl-3-methyl-1-penten-3-ol ( 7) and 5-acetoxy-3-(3-hydroxy-3-methylpent-4-enyl)-2,4,4-trimethylcyclohex-2-enone ( 8) were prepared from 6,7-epoxygeranyl acetate ( 9), via (2′,5′-epoxy-2′,6′,6′-trimethyl)cyclohexylmethyl tosylate ( 10), for the first time. 5 is an intermediate in the synthesis of the sesquiterpene-coumarin ether (±)-farnesiferol C ( 1). The preparation of suitable intermediates for synthesising related natural farnesiferol B ( 3) and D ( 4) is also reported.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(00)00560-3