Total synthesis of (+)??13??ethyl??3??methoxygona??1, 3, 5, 9 (11)??tetraen??17??one via the tandem Claisen??ene strategy

EM Groen??Piotrowska, MB Groen

Index: Groen-Piotrowska, E. M.; Groen, M. B. Recueil des Travaux Chimiques des Pays-Bas, 1993 , vol. 112, # 12 p. 627 - 634

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Citation Number: 11

Abstract

Abstract A total synthesis of the title compound 2, a potential precursor of the progestagens desogestrel and 3-ketodesogestrel, is described. The backbone of the steroid was assembled by condensation of 1, 2-dihydro-4, 7-dimethoxynaphthalene (12) and [S-(Z)]-8, 9- dihydroxy-7-ethyl-6-nonen-2-ynoic acid methyl ester 9-(tert-butyldimethyl) silyl ether (11), prepared from [R-(+)]-glyceraldehyde acetonide (4), and subsequent Claisen ...