A Concise, Enantioselective Synthesis of (−)- and (+)-Hongconin
Citations Over TimeTop 10% of 1996 papers
Abstract
Optically pure enone 9c, available in three steps from known 6-deoxy D-galactal derivative 7b, reacts with cyanophthalide 6 to directly afford the natural product (-)-hongconin (1), a compound from traditional Chinese medicine recently shown to exhibit antianginal activity. The enantiomer of 1 and its (+)-cis-diastereomer were also synthesized in a parallel fashion from the L-sugar counterpart. The use of C-glycoside Michael acceptors, as opposed to their O-glycoside counterparts, represents a potentially useful simplification of phthalide annulation methodology in synthesizing numerous other such optically pure isochromanquinoids, since it obviates the inconvenience of additional steps late in the synthetic scheme associated with reductive manipulation of a remaining acetal moiety into the desired pyran ring substituent.
Related Papers
- → Use of Stabilized Phthalide Anion Annulation Reactions in Synthesis: An Update(2007)30 cited
- → Anthracyclines. XVI. Further Comments Concerning the Phthalide Anion Annelation of Quinone Monoacetals(1987)16 cited
- → Phthalide Derivatives from Meum athamanticum Jacq(1984)4 cited
- → Synthesis of Pyranonaphthoquinone Antibiotics Involving the Phthalide Annulation Strategy(2006)3 cited
- Synthesis of 3-(3-hydroxypropyl)-phthalide and pedicellosine(1999)