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Paper | Regular issue | Vol 63, No. 6, 2004, pp.1359-1374
Published online, 9th April, 2004
DOI: 10.3987/COM-04-10057
Intramolecular Pauson-Khand Reaction of 3-Alkynyl-1-alkylidenecycles: A Convenient Synthesis of [5.n.1.01,5] Tricyclic Compounds

Miyuki Ishizaki,* Mina Masamoto, Osamu Hoshino, Kiyoshi Nishitani, and Hiroshi Hara*

*Faculty of Pharmaceutical Sciences, Science University of Tokyo, 2641 Yamazaki, Noda, Chiba 278-8510, Japan


An intramolecular Pauson-Khand reaction of various 3-alkynyl-1-alkylidenecyclic compounds was performed to give the corresponding [5.n.1.01,5] tricyclic compounds (n = 2-4). A facile construction of the core structure in cedrene terpenoids was also investigated in detail and formal total synthesis of α- and β-cedrenes was accomplished.