Total synthesis of (.+-.)-pentalenene, the least oxidized neutral triquinane metabolite of Streptomyces griseochromogenes

LA Paquette, GD Annis

文献索引：Paquette,L.A.; Amis,G.D. Journal of the American Chemical Society, 1983 , vol. 105, p. 7358

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被引用次数: 47

摘要

Abstract: Pentalenene, the neutral precursor to pentalenic acid and a variety of pentalenolactones, has been synthesized from 4, 4-dimethyl-2-cyclopentenone. Following hydrosilation, dichloroketene addition, and hydrolysis, ring expansion to the highly functionalized bicyclo [3.3. 0] octanone 22 was achieved with diazomethane. Reduction with zinc and acetic acid led to regiospecific a-chloro enone formation. In six additional steps, ...