Tetrahedron

Synthesis of a caryophyllene isoprenologue, a potential diterpene natural product

SFR Hinkley, NB Perry, RT Weavers

Index: Hinkley, Simon F.R.; Perry, Nigel B.; Weavers, Rex T. Tetrahedron, 2005 , vol. 61, # 15 p. 3671 - 3680

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Citation Number: 4

Abstract

(−)-β-Caryophyllene has been converted into three stereoisomers of a new bicyclic compound that is structurally related to the known macrocyclic diterpene, flexibilene, in the same way β-caryophyllene is related to humulene. Key steps are selective cleavage of caryophyllene, addition of a five carbon component by a Wittig reaction and McMurry cyclization.