Total synthesis of (.+-.)-poitediol and (.+-.) 4-epipoitediol

RC Gadwood, RM Lett…

Index: Gadwood; Lett; Wissinger Journal of the American Chemical Society, 1984 ,  vol. 106,  # 13  p. 3869 - 3870

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Citation Number: 34

Abstract

lowed by acetylation and elimination afforded cyclopentene 4. Further reduction and methylation of the resulting alcohol produced 5. Ozonolysis (Me2S workup) and cyclization of the resulting keto aldehyde led to cyclohexenone 6. Stereoselective reduction of 6 with DIBAH in Et20 at-100 OC6 gave a diastereomeric mixture, which was cy~ lopropanated~ to afford a separable mixture of norcaranols 7a and 7b (8: l ratio). 8 Oxidation of 7a and ...