TOTAL SYNTHESIS OF SPORIDESMIN-A
TOTAL SYNTHESIS OF SPORIDESMIN-A
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DOI：
10.1021/ja00800a079
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发表时间：
1973-01-01
影响因子：
15
通讯作者：
HAVEL, M
中科院分区：
文献类型：
--
作者：
KISHI, Y;NAKATSUKA, S;HAVEL, M
H, s), and 4.00 (3 H, s)] which was oxidized with iodo-sobenzene diacetate in acetonitrile containing dimethyl sulfide, to afford the cyclized diacetate 14a3b'n [amorphous solid; M+(found) 677.1288 and 679.1266,(cald) 677.1268 and 679.1239;£ 13 (1.2 mg in 0.3 ml) 1.63 (3 H, s), 1.95 (3 H, s), 2.01 (3 H, s), 3.02 (3 H, s), 3.51 (3 H, s), 3.80 (3 H, s), 3.86 (3 H, s), 3.87 (3 H, s)] 12 in 30% yield. 11· 13 The two new asymmetric centers introduced in this step are expected to be desired ones for the steric reasons. The synthetic diacetate 14a was identified by com-parison of spectroscopic data (nmr, ir, uv, and mass spectral) 12 as well as tic behavior with the authentic di-acetate 14a, which was prepared from natural spo-ridesmin A (l) 14 in threesteps: sodium borohydride reduction in methanol, anisaldehydetreatment in methylene chloride containing boron trifluoride etherate, and acetylation with acetic anhydride and pyr-idine. 15The authentic diacetate 14a was successfully con-verted back to sporidesmin A (1) in 25% overall yield in three steps: sodium hydroxide in aqueous methanol at room temperature, m-chloroperbenzoic acid in methylene chloride at room temperature, and boron trifluoride etherate in methylene chloride at room tem-
