A partial synthesis of (-)-shinjulactone H from (+)-quassin

H Nakamura, S Vasudevan, M Kim…

Index: Nakamura, Hideo; Vasudevan, Sundar; Kim, Moonsun; Brock, Carolyn P.; Watt, David S. Journal of Organic Chemistry, 1992 , vol. 57, # 8 p. 2223 - 2227

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Citation Number: 5

Abstract

A partial synthesis of (-)-shinjulactone H (3) from (+)-quasin (1) required the selective manipulation of two similar 0-methyldiosphenol groups. Protection of the &lactone in 1 as an ortho ester, selective reduction of the C-1 carbonyl group, hydrolysis of the resulting enol ether in the A ring, and catalytic hydrogenation of the 0-methyldiosphenol in the C ring delivered an intermediate possessing an a-keto1 group in the A ring and an a-methoxy ...