Regio-and Stereoselective Cyclopentannulation with Ketones and Propargyl Alcohol Derivatives. Synthesis of dl-Nootkatone and dl-Muscopyridine

T Hiyama, M Shinoda, H Saimoto…

Index: Hiyama, Tamejiro; Shinoda, Masaki; Saimoto, Hiroyuki; Nozaki, Hitosi Bulletin of the Chemical Society of Japan, 1981 , vol. 54, # 9 p. 2747 - 2758

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Citation Number: 29

Abstract

A highly regio-and stereoselective five-membered ring annulation involving the acid- treatment of propargyl alcohol dianion adducts of ketones is described. The propargyl alcohol adduct of 2-octanone was converted into 2-methyl-3-pentyl-2-cyclopentenone by treatment with sulfuric acid–methanol (1: 1) at 0° C. As the major product, 1-methylbicyclo [5.3. 0] dec-6-en-8-one was produced from 2-methylcycloheptanone. Remarkable ...