Total synthesis of (+)-tanikolide, using regioselective elimination of a vicinal dibromoalkane

Total synthesis of (+)-tanikolide, using regioselective elimination of a vicinal dibromoalkane
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DOI:
10.1246/bcsj.78.1549
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发表时间:
2005-08-15
影响因子:
4
通讯作者:
Nishiyama, S
Nishiyama, S
中科院分区:
化学3区
文献类型:
--
作者:
Ohgiya, T;Nakamura, K;Nishiyama, S

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以相应的1-酰氧基-2,3-二溴代烷为原料,通过区域选择性和温和的HBr消除反应,结合钯介导的C-C偶联反应和夏普莱斯不对称环氧化反应,成功地合成了海洋来源的具有生物活性的三角洲-内酯(+)-tanikolide。
Total synthesis of (+)-tanikolide, a bioactive delta-lactone of marine origin, was successfully accomplished by utilizing a bromoalkene derivative conveniently synthesized from the corresponding 1-acyloxy-2,3-dibromoalkane by the regioselective and mild HBr-elimination reaction, along with the Pd-mediated C-C coupling reaction and the Sharpless asymmetric epoxidation as key steps.