Ring Contraction of Cyclobutanes and a Novel Cascade Reaction: Application to Synthesis of (.+-.)-Anthoplalone and (.+-.)-Lepidozene

…, T Taniguchi, Y Tokunaga, K Fukumoto

Index: Ihara; Taniguchi; Tokunaga; Fukumoto Journal of Organic Chemistry, 1994 , vol. 59, # 26 p. 8092 - 8100

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Citation Number: 27

Abstract

Two efficient and practical synthetic methodologies for the construction of small ring systems have been developed. The fist method involves a novel rearrangement of cyclobutanes 10 and 14 leading to cyclopropanes 11 and 15 employing BF3OEt2 or POC13 in the presence of pyridine or Raney nickel. The second method utilizes a novel cascade reaction of a, P- unsaturated esters 25 and 36 possessing a cyclopropyl ketone moiety with TMSI in the ...