Lewis acid promoted decomposition of unsaturated. alpha.-diazo ketones. 1. An efficient approach to simple and annulated cyclopentenones

AB Smith III, BH Toder, SJ Branca…

Index: Smith,A.B.; Toder,B.H.; Branca,S.J. Journal of the American Chemical Society, 1981 , vol. 103, p. 1996

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Citation Number: 41

Abstract

(24). Method A. Hydroxyketone 23 (38 mg) was dissolved in benzene (25 mL) to which aluminum chloride (67 mg, 0.5 mmol) was added. The reaction mixture was stirred at room temperature for 16 h and poured into water. The benzene extract was evaporated. Recrystallization of the residue from methanol afforded red needles of 4-demethoxy-7- deoxydaunomycinone (24)(33 mg, 94%): mp 160-162 OC (lit.,'mp 160-162" C); NMR 6 ...

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