4283-48-1Relevant articles and documents
A Partial Synthesis of (-)-Shinjulactone H from (+)-Quassin
Nakamura, Hideo,Vasudevan, Sundar,Kim, Moonsun,Brock, Carolyn P.,Watt, David S.
, p. 2223 - 2227 (2007/10/02)
A partial synthesis of (-)-shinjulactone H (3) from (+)-quassin (1) required the selective manipulation of two similar O-methyldiosphenol groups.Protection of the δ-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 O-methyldiosphenol in the C ring delivered an intermediate possessing an α-ketol group in the A ring and an α-methoxy ketone group in the C ring.Demethylation and concomitant α-ketol tautomerization in the A ring delivered (-)-shinjulactone H (3).