Transannular Hetero Diels-Alder Reaction of Macrocyclic α,β-Unsaturated Thioketones and Synthesis of Oxonin Derivatives by Desulfurization of the Transannular Adducts

Satoshi Moriyama; Takayuki Karakasa; Takashi Inoue; Katsumi Kurashima; Sadayoshi Satsumabayashi; Takao Saito

doi:10.1055/s-1996-5330

Synlett 1996; 1996(1): 72-74
DOI: 10.1055/s-1996-5330

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Transannular Hetero Diels-Alder Reaction of Macrocyclic α,β-Unsaturated Thioketones and Synthesis of Oxonin Derivatives by Desulfurization of the Transannular Adducts

Satoshi Moriyama, Takayuki Karakasa, Takashi Inoue, Katsumi Kurashima, Sadayoshi Satsumabayashi, Takao Saito^*

^*Department of Chemistry, Faculty of Science, Science University of Tokyo (SUT), Shinjuku-ku, Tokyo 162, Japan, Fax 81-3-3235-2214; E-mail tsaito@ch.kagu.sut.ac.jp

Abstract

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Macrocyclic α,β-unsaturated thioketones 2 generated by thionation of the corresponding ketones 1, readily underwent the transannular hetero Diels-Alder reaction highly stereoselectively to yield the trans-fused cycloadducts 3, which were converted into the oxonin derivatives 5 via reductive desulfurization with Raney nickel.

transannular hetero Diels-Alder reaction - α,β-unsaturated thioketones - oxonin - reductive desulfurization - ring expansion

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