HCID 69893717, compound → HCID 12990580, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 0.30 g (1.1 mmol) of lactols 9S and 9R in 15 mL of benzene under argon was added 0.60 g (1.3 mmol) of lead tetraacetate. After the mixture was stirred at 25° C. for 4 h, it was diluted with diethyl ether, the organic layer was washed with water, and brine, dried (MgSO4), concentrated, and column chromatographed on silica gel using a gradient mixture of hexane and diethyl ether as eluent to give 0.25 g (85% yield) of aldehyde 11. [α]22D=−54.4° (c 0.25, CHCl3); 1H NMR (CDCl3) δ 9.98 (d, J=4Hz, 1H, CHO), 7.92 (s, 1H, OCHO), 2.55 (dd, J=9.6, 3.2Hz, 1H, C4a-H), 2.49 (d, J=4Hz, 1H, C1-H), 1.85 (s, 3H, Me), 1.84˜0.90 (m, 10H), 1.18 (s, 3H, Me), 0.89 (s, 3H, Me), 0.83 (s, 3H, Me); 13C NMR (CDCl3) δ 204.2 (C═O), 160.1 (C═O), 85.9, 68.9, 55.1, 41.7, 40.0, 39.9, 39.1, 33.4, 22.3, 21.6, 21.5, 20.0, 18.1, 17.2.

Provenance & Evidence