Monocrotaline → (3R,4R,5R,13aR)-4,5,8,12,13,13a-Hexahydro-4,5-dihydroxy-3,4,5-trimethyl-2H-(1,6)dioxacycloundecino(2,3,4-gh)pyrrolizine-2,6(3H)-dione

Participants

Reaction Conditions

Reaction Steps

To monocrotaline (20 mg) dissolved in chloroform (5 mL) was added a solution of o-chloranil (25 mg) in chloroform (5 mL). After 5 min, TLC (Thin layer Chromatography) showed that most of starting material was consumed and the mixture was shaken vigorously with a cooled (0-5° C.) solution, which contained 700 mg KOH and 20 mg NaBH4 in 1 mL water for 10-15 sec. The organic phase was separated, immediately dried with anhydrous Na2SO4 and concentrated under reduced pressure to give dehydromonocrotaline (DHM). The chemical reaction was depicted in FIG. 21.

Provenance & Evidence