Sodium Benzoate → (+)-Pancratistatin

Participants

Reaction Conditions

Reaction Steps

A suspension of epoxide 16 (109 mg, 0.21 mmol) and sodium benzoate (1 mg) in water (8 ml) was stirred at 100° C. for 6 days. The mixture was then concentrated and subjected to chromatography (CHCl3 /CH3OH, 4:1) to afford 35 mg (51%) of pancratistatin. 1H NMR (400 MHz, DMSO-d6) ε 13.06 (s, 1H), 7.51 (s, 1H), 6.48 (s, 1H), 6.05 (d, J=1.0 Hz, 1H), 6.02 (d, J=1.0 Hz, 1H), 5.35 (bs, 1H), 5.04 (bs, 2H), 4.84 (bs, 1H), 4.27 (bs, 1H), 3.95 (bs, 1H), 3.84 (bs, 1H), 3.74 (m, 2H), 2.96 (d, J=11.5 Hz, 1H).

Provenance & Evidence