中環状チオノカルボナートの[3,3]シグマトロピー転位を経由した環拡大反応
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概要
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A highly stereoselective synthesis of (<I>Z</I>) - or (<I>E</I>) -double bonds in 10-membered thiolcarbonates is achieved by the [3, 3] sigmatropic rearrangement of 8-membered thionocarbonates which proceeds through the chairlike vs. boatlike transition states. The formation of the 8-membered intermediates followed by their [3, 3] sigmatropic rearrangements were investigated by experiments and theoretical calculations. Their utilities of this methodology have been demonstrated by the unique and stereoselective synthesis of (-)-yellow scale pheromone. Moreover, medium-membered heterocyclic allenes were synthesized by this method. The structure and reactivity of a new type of strained 8-membered allene were also examined. Using this method combined with a novel application of the newly developed SmI<SUB>2</SUB>-HMPA reduction of the cyclic allene, the antifungal constituent of a <I>Sapium japonicum</I> was synthesized.
- 社団法人 有機合成化学協会の論文
- 1995-08-01
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