Issue 12, 2017

Total synthesis of orientalol F via gold-catalyzed cycloisomerization of alkynediol

Abstract

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.

Graphical abstract: Total synthesis of orientalol F via gold-catalyzed cycloisomerization of alkynediol

Supplementary files

Article information

Article type
Research Article
Submitted
28 Jul 2017
Accepted
23 Aug 2017
First published
25 Aug 2017

Org. Chem. Front., 2017,4, 2296-2300

Total synthesis of orientalol F via gold-catalyzed cycloisomerization of alkynediol

Y. Gu, J. Huang, J. Gong and Z. Yang, Org. Chem. Front., 2017, 4, 2296 DOI: 10.1039/C7QO00654C

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements