Cyclopentene annulation via intramolecular addition of diazoketones to 1, 3-dienes. Applications to the synthesis of cyclopentanoid terpenes

T Hudlicky, FF Koszyk, TM Kutchan…

Index: Hudlicky, Tomas; Koszyk, Francis J.; Kutchan, Toni M.; Sheth, Jagdish P. Journal of Organic Chemistry, 1980 , vol. 45, # 25 p. 5020 - 5027

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Citation Number: 125

Abstract

Initial model studies investigating the utility of a new intramolecular cyclopentene annulation procedure are described as pertaining to the preparation of bicyclo [3.3. 0]~ nones. Several l- b5, 7-octadien-2-ones substituted at the I-, 7-, or &position were decomposed in the presence of C u (a~ ac)~ to yield stereospecifically the corresponding vinylcyclopropanes 13, 16, 21, 24, and 27. The thermal as well as the rhodium-promoted modes of ...