Tetrahedron

Bisannelation with Vinylselenoxide: Synthesis of Tricyclo [3.2. 1.0 2, 7] octane-6-one and its Congeners

H Hagiwara, H Sakai, M Kirita, T Hoshi, T Suzuki…

Index: Hagiwara, Hisahiro; Sakai, Hitoshi; Kirita, Miki; Hoshi, Takashi; Suzuki, Toshio; Ando, Masayoshi Tetrahedron, 2000 , vol. 56, # 11 p. 1445 - 1449

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Citation Number: 11

Abstract

As a part of our synthetic study towards such natural products, we wish to disclose a new synthetic protocol towards tricyclo[3.2.1.0 2,7 ]octane-6-one derivatives 10, formed as a result of domino Michael–Michael-substitution reaction involving the kinetically derived enolate 2 of cyclohexenone 1 with vinylselenoxide 3 in a single pot operation (Scheme 1). ... If proton transfer from the anion 4 to 5 is suppressed, we expected that successive intramolecular Michael reaction of ...