TOTAL SYNTHESIS OF (-)-COLLETOL

TOTAL SYNTHESIS OF (-)-COLLETOL
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DOI:
10.1021/jo00023a029
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发表时间:
1991-11-08
影响因子:
3.6
通讯作者:
MURRY, JA
MURRY, JA
中科院分区:
化学2区
文献类型:
--
作者:
KECK, GE;MURRY, JA

文献摘要

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首次全合成了不对称双大环内酯(-)-Colletol。 该合成涉及刘易斯酸介导的三苯基烯丙基锡烷加成到醛14上以设定C12立体化学。 倒数第二步利用大环内酯化来组装14元环。 天然产物经12步线性反应制得,总收率12%。
The first total synthesis of the unsymmetrical bis-macrolide (-)-colletol is described. The synthesis involves a Lewis acid mediated addition of triphenylallylstannane to aldehyde 14 to set the C12 stereochemistry. The penultimate step utilized macrolactonization to assemble the 14-membered ring. The natural product was prepared in 12 linear steps and 12% overall yield.