Abstract
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).
Original language | English |
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Pages (from-to) | 2223-2227 |
Number of pages | 5 |
Journal | Journal of Organic Chemistry |
Volume | 57 |
Issue number | 8 |
DOIs | |
State | Published - Apr 1 1992 |
ASJC Scopus subject areas
- Organic Chemistry