Syntheses of ( + )-Phrymarolin II and Its Stereoisomers

1 December 1986

journal article
research article
Published by Oxford University Press (OUP) in Agricultural and Biological Chemistry

Vol. 50 (12) , 3119-3125
https://doi.org/10.1080/00021369.1986.10867871

Abstract

Phrymarolin II, a unique naturally-occurring lignan having a 1,2-dioxygenated 3,7-dioxabicyclo[3.3.0]octane skeleton, was synthesized by the reaction of sesamol, in the presence of cadmium carbonate, with 1-acetoxy-2-chloro-6-(2′-methoxy-4′,5′-methylenedioxyphenyl)-3,7-dioxabicyclo[3.3.0]octane. The latter was prepared through 13 steps starting from an aldol condensation of β-vinyl-γ-butyrolactone with 2-methoxy-4,5-methylenedioxybenzaldehyde. Three diastereomers of phrymarolin II were also obtained.

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