A New Approach to the Synthesis of Long??Chain Polypropionates Based on the Diels??Alder Monoadditions of 2, 2′??Ethylidenebis [3, 5??dimethylfuran]

J Ancerewicz, P Vogel

Index: Ancerewicz, Jacek; Vogel, Pierre Helvetica Chimica Acta, 1996 , vol. 79, # 5 p. 1393 - 1414

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Citation Number: 24

Abstract

Abstract Acidic condensation of 2, 4-dimethylfuran with acetaldehyde provided 2, 2′- ethylidenebis [3, 5-dimethylfuran](7) which added 1 equiv. of methyl bromopropynoate to give a major adduct 8. Regio-and stereoselective hydroboration of the latter 7- oxanorbornadiene derivative followed by alcohol protection and methanolysis of its β- bromoacrylate moiety gave (1RS, 2RS, 4RS, 5SR, 6SR, 1′ RS)-methyl 4-[1′-(3 ″, 5 ″- ...