Abstract
The anions of 3-cyano- or 3-(phenylthio)phthalide react with Michael acceptors to afford functionalized naphthydroquinones in good yield. The cyano and phenylthio groups function both as activating groups and as leaving groups. An alternative involves the use of protected o-(carboxymethyl)cyanohydrins. The use of phthalide anions in synthesis is exemplified by total syntheses of kalafungin, pachybasin, and chrysophanol. This methodolgy constitutes a direct and regiospecific approach to polycyclic systems.
Original language | English |
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Pages (from-to) | 3439-3444 |
Number of pages | 6 |
Journal | Journal of Organic Chemistry |
Volume | 48 |
Issue number | 20 |
DOIs | |
Publication status | Published - 1983 Oct |
Externally published | Yes |
ASJC Scopus subject areas
- Organic Chemistry