Stereoselective Synthesis of Steroids and Related Compounds, V. Synthesis of (±)??Chokol A by a Tandem Michael??Addition/Dieckmann Cyclization

…, W Halfbrodt, T Köhler, P Kreye

Index: Groth, Ulrich; Halfbrodt, Wolfgang; Koehler, Thomas; Kreye, Paul Liebigs Annalen der Chemie, 1994 , # 9 p. 885 - 890

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Citation Number: 11

Abstract

Abstract A total synthesis of (±)-chokol A (rac-12) was accomplished in five steps by starting from the α, β-unsaturated ester (E)-2 in an overall yield of 24%. The key step of this synthesis is the tandem conjugate addition/Dieckmann cyclization of the cuprate derived from vinyl bromide 9 with the α, β-unsaturated ester (E)-2.