First total syntheses of (3 R,5 R)-sonnerlactone and (3 r,5 s)-sonnerlactone

Article abstract of DOI:10.1055/s-0031-1289529

First total syntheses of the macrocyclic natural products (3R,5R)-sonnerlactone and (3R,5S)-sonnerlactone, two new metabolites isolated from the endophytic fungus strain Zh6-B1, have been accomplished in eleven steps with 22% overall yield starting from enantiomerically pure (R)-propylene oxide prepared by hydrolytic kinetic resolution. Other key steps are Sharpless epoxidation, reductive elimination of iodo epoxide, and ring-closing-metathesis reaction for the construction of the macrolactone. Georg Thieme Verlag Stuttgart · New York.