Total synthesis of orientalol F via gold-catalyzed cycloisomerization of alkynediol,Organic Chemistry Frontiers

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Total synthesis of orientalol F via gold-catalyzed cycloisomerization of alkynediol
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2017-08-25 00:00:00 , DOI: 10.1039/c7qo00654c
Yueqing Gu _{1,

2,

3,

4,

5} , Jun Huang _{1,

2,

3,

4,

5} , Jianxian Gong _{1,

2,

3,

4,

5} , Zhen Yang _{1,

2,

3,

4,

5}

Affiliation

The total synthesis of orientalol F has been achieved starting from 1,4-dioxaspirodecan-8-one 11 in 13 steps. The key steps in this synthesis feature: (1) gold-catalyzed tandem cycloisomerization of alkynediol 10 for the formation of its seven-membered oxa-bridged bicyclic skeleton 9 of orientalol F, (2) visible-light-promoted organocatalytic aerobic oxidation of silyl enol ether 16 to enone 17, (3) Barbier-type butenylation for the diastereoselective synthesis of allylic alcohol 18 from enone 17, and (4) substrate-controlled Pd-catalyzed hydrogenation of 20 for the stereoselective installation of the C1 stereogenic center of 8.

中文翻译：

通过炔烃二醇的金催化环异构化全合成东方酚F

从1，4-二氧杂螺环烷-8-one 11开始，在13个步骤中完成了香酚F的全合成。该合成的关键步骤包括：（1）炔二醇10的金催化串联环异构化反应，以形成其七元酚F的七元氧桥双环骨架9；（2）可见光促进的甲硅烷基的有机催化需氧氧化烯醇醚16至烯酮17，（3）Barbier型丁烯化，用于从烯酮17非对映选择性合成烯丙醇18，以及（4）底物控制的Pd催化的20的氢化，以立体选择性地安装C1立体异构中心8。

更新日期：2017-09-04

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