Helvetica chimica acta

Synthesis of the 2??Alkenyl??4??alkylidenebut??2??eno??4??lactone (= α??Alkenyl?螃摸?alkylidenebutenolide) Core Structure of the Carotenoid Pyrrhoxanthin via the …

J Schmidt??Leithoff, R Brückner

Index: Schmidt-Leithoff, Joachim; Brueckner, Reinhard Helvetica Chimica Acta, 2005 , vol. 88, # 7 p. 1943 - 1959

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Citation Number: 10

Abstract

Abstract A new strategy for the stereoselective synthesis of 4-alkylidenebut-2-eno-4-lactones (= γ-alkylidenebutenolides) with (Z)-configuration of the exocyclic C [DOUBLE BOND] C bond at C (4) was developed. It is exemplified by the synthesis of 4-alkylidenebutenolactone 31 (Scheme 4), which constitutes a substructure of the carotenoids pyrrhoxanthin (1) and peridinin. The formation of the precursor 4-(1-hydroxyalkyl) butenolactone 29 was ...