A reactive lactonic dienophile-3-carbethoxy-5, 5-dimethyl-2 (5 H)-furanone. Application to the synthesis of a monoterpenoid lactone

…, ENC Browne, PR Pednekar

Index: Liu, Hsing-Jang; Browne, Eric N. C.; Pednekar, Purushottam R. Canadian Journal of Chemistry, 1982 , vol. 60, p. 921 - 925

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Citation Number: 16

Abstract

In contrast to the low dienophilicity generally observed for α, β-unsaturated lactones, the title compound 2 is shown to be a reactive dienophile. Under stannic chloride catalysis, it undergoes Diels-Alder reaction region-and stereoselectively with a variety of dienes at room temperature. The synthesis of (±)-o-mentha-1, 3-dien-1→ 8-olide (20) has been achieved by a two-step sequence using lactone ester 2. Addition of 2 to 1-acetoxy-1, 3-butadiene ...