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【结 构 式】 
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【分子编号】36930 【品名】 【CA登记号】 |
【 分 子 式 】C28H39N2O3 【 分 子 量 】451.62934 【元素组成】C 74.47% H 8.7% N 6.2% O 10.63% |
合成路线1
该中间体在本合成路线中的序号：(XVII)Intermediate (XV) is submitted to cyclization by means of trifluoroacetic anhydride (TFAA) and TEA in DMSO furnishing the spiranic 1,4-diazabicyclo[3.2.1]heptane derivative (XVI). The oxidation of (XVI) with DDQ in dichloromethane provides eniminium salt (XVII), which is reduced with NaCNBH3 to affords the butyleneketal of the target compound that is deprotected with HCl in aqueous acetone.
| 【1】 Lin, H.; Snider, B.B.; Biomimeric total syntheses of (-)-TAN1251A, (+)-TAN1251B, (+)-TAN1251C, and (+)-TAN1251D. Org Lett 2000, 2, 5, 643. |
合成路线2
该中间体在本合成路线中的序号：(XVII)Intermediate (XV) is submitted to cyclization by means of trifluoroacetic anhydride (TFAA) and TEA in DMSO furnishing the spiranic 1,4-diazabicyclo[3.2.1]heptane derivative (XVI). The oxidation of (XVI) with DDQ in dichloromethane provides eniminium salt (XVII), which is reduced with NaCNBH3 to afford the butyleneketal intermediate that is deprotected with HCl in aqueous acetone yielding the TAN-1251a (XVIII). Finally, this compound is treated with LDA in THF giving a mixture of enolates that is quenched with TMSCl. This mixture of silyl enolates is oxidized with OsO4 in aqueous tert-butanol yielding a mixture of hydroxylated compounds that is resolved by a cumbersome chromatographic separation on a reverse phase HPLC column, followed by a chiral Chiralpak AD column.
| 【1】 Lin, H.; Snider, B.B.; Biomimeric total syntheses of (-)-TAN1251A, (+)-TAN1251B, (+)-TAN1251C, and (+)-TAN1251D. Org Lett 2000, 2, 5, 643. |