Desymmetrization of Hepta-1,6-dien-4-ol by Prins Reaction and Subsequent Cross-Metathesis: Access to Diospongine A Homologues

Abstract

A new tetrahydropyran scaffold has been efficiently prepared by Prins reaction between hepta-1,6-dien-4-ol and benzaldehyde. Subsequent functionalizations were further achieved by Mitsunobu reaction and/or by the way of cross-metathesis/Wacker oxidation sequence to deliver diospongin A analogues.

Synthesis of diospongin A, ent-diospongin A and C-5 epimer of diospongin B from tri-O-acetyl-D-glucal

“…Since the first asymmetric total synthesis of diospongins A and B carried out in 2006 by Jennings and co-workers, 2 several total syntheses of 1 and 2 and their enantiomers have been developed. [3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20] …”