The Journal of Organic Chemistry

Cobalt-mediated [2+ 2+ 2] cycloadditions en route to natural products: A novel total synthesis of steroids via the one-step construction of the B, C, D framework from an …

ED Sternberg, KPC Vollhardt

Index: Sternberg, Ethan D.; Vollhardt, K. Peter C. Journal of Organic Chemistry, 1982 , vol. 47, # 18 p. 3447 - 3450

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Citation Number: 35

Abstract

The first application of the cobalt-mediated intramolecular cyclization of a&-diynenes to annulated cyclohexadienes in natural product synthesis is described by demonstrating its feasibility in a versatile and efficient steroid synthesis, including a new total synthesis of the Torgov intermediate, 3-methoxyestra-l, 3, 5 (10), 8, 14-pentaen-17-one, via a new steroid, 3- methoxyestra-1, 3, 5 (10), 8 (14), 9-pentaen-17-one ethylene ketal. Several model ...