Tetrahedron Letters p. 197 - 200 (1989)
Update date:2022-07-30
Topics:
Tokoroyama, Takashi
Pan, Li-Rui
The Hosomi-Sakurai reactions of E- and Z-crotylsilanes with cyclohexenone at -78 degC showed respectively high erythro and relatively low threo selectivities, modification of the silyl substituents giving a variable effect.In the reaction with Z-alkoxycrotylsilanes, the threo selectivity could be improved by the utilization of the kinetic difference between the diastereomeric products 4 and 5 to the secondary cyclization.Starting from 4 and 5 thus obtained, the syntheses of both (+/-)-juvabione and (+/-)-epi-juvabione have been respectively achieved in a concise way.
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(1989)
