HCID 70465682, compound → HCID 57027331, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the chlorodiester (10) (730 mg, 1.1 mmol) in ether (15 ml) lithium aluminium hydride (48 mg) was added and the mixture was stirred at 0° C. for 1 hr. and then stirred at room temperature for 2 hr. The usual work-up (ether for extraction) gave a crude product, which was applied to a column of silica gel (50 g). Elution with dichloromethane provided the chlorodiol (11) (250 mg, 39%) mp 152°-153° C. (n-hexane-ether). 1H-NMR δ(CDCl3 -acetone d6 -DMSO d6): 0.77 (3H, s, 18-H3), 1.00 (3H, s, 19-H3), 1.10 (3H, d, J=6 Hz, 21-H3), 3.50-4.50 (7H, m, 3-H, 26-H2, 27-H2, and THP), 4.77 (3H, m, 26-OH 27-OH and THP), 5.38 (1H, m, 6-H); δ(CDCl3 -acetone d6 -DMSOd6 -D2O): 3.60 (2H, m, THP), 3.77 (4H, s, 26-H2 and 27-H2), 4.77 (1H, m, THP). MS m/z: 434, 416, 404. Anal. Calcd for C32H51O4ClF2 : C, 67.05; H, 8.97; Cl, 6.19; F, 6.63. Found: C, 67.08; H, 8.89; Cl, 5.99; F, 6.53.

Provenance & Evidence