Comprehensive synthetic route to eight diastereomeric Podophyllum lignans

…, D Rajapaksa, NJ Taylor, R Rodrigo

Index: Forsey, Steven P.; Rajapaksa, Dayananda; Taylor, Nicholas J.; Rodrigo, Russell Journal of Organic Chemistry, 1989 , vol. 54, # 18 p. 4280 - 4290

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Citation Number: 77

Abstract

An oxabicyclo compound, 9, prepared in 47% yield through an isobenzofuran intermediate was converted with excellent regio-and stereocontrol to eight (i)-lignan lactones of the podophyllotoxin series. One of the eight, epiisopicropodophyllin, 36, the 1, 2, 3, 4-cis isomer, previously unknown, was prepared as its methyl ether, 37. A comparative study of the'H NMR spectra of all eight lactones aided by an X-ray crystal structure of a 2, 3-cis lactone, ...