A Partial Synthesis of (−)-Shinjulactone H from (+)-Quassin

Hideo Nakamura, Sundar Vasudevan, Moonsun Kim, Carolyn P. Brock, David S. Watt

Research output: Contribution to journalArticlepeer-review

4 Scopus citations


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 languageEnglish
Pages (from-to)2223-2227
Number of pages5
JournalJournal of Organic Chemistry
Issue number8
StatePublished - Apr 1 1992

ASJC Scopus subject areas

  • Organic Chemistry


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