Synlett

A Convenient Transformation of 2-Alkylidenecycloalkanones into Alkyl-Substituted Bicyclo [n. 1.0] alkan-1-ols: Application to the Synthesis of Capsaicin

DG Kananovich, DM Zubrytski, OG Kulinkovich

Index: Kananovich, Dzmitry G.; Zubrytski, Dzmitry M.; Kulinkovich, Oleg G. Synlett, 2010 , # 7 p. 1043 - 1046

Full Text: HTML

Citation Number: 1

Abstract

Abstract Treatment of 2-alkylidenecycloalkanones with hydrogen iodide in benzene and subsequent reaction of the obtained β-iodo ketones with zinc dust in THF in the presence of chlorotrimethylsilane or titanium (IV) chlorotriisopropoxide led to exo-and endo-(n+ 3)- alkylbicyclo [n. 1.0] alkan-1-ols in high yields. Cyclization of the intermediate β-iodo ketones under these conditions proceeded in a moderate to good diastereoselectivity, and the ...