Enantioselective total synthesis of sagittacin E and related natural products

Hideki Abe; Mitsuru Fujimaki; Eri Nakagawa; Toyoharu Kobayashi; Hisanaka Ito

doi:10.1039/C8CC03438A

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

Enantioselective total synthesis of sagittacin E and related natural products†

Hideki Abe,

*^ab Mitsuru Fujimaki,^a Eri Nakagawa,^a Toyoharu Kobayashi

^a and Hisanaka Ito*^a

Author affiliations

* Corresponding authors

^a School of Life Sciences, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan

^b Department of Chemical and Biological Sciences, Faculty of Science, Japan Women's University, 2-8-1 Mejirodai, Bunkyo-ku, Tokyo 112-8681, Japan

Abstract

The first enantioselective total synthesis of eremophilane-type sesquiterpenoids, sagittacin E and related natural products, was achieved. This synthesis features an asymmetric desymmetrization by Shi asymmetric epoxidation, intramolecular aldol-type cyclization, allylic oxidation of a 1,4-diene compound, and stereoselective epoxidation.

This article is part of the themed collection: Natural product synthesis

Download options Please wait...

Supplementary files

Article information

DOI: https://doi.org/10.1039/C8CC03438A
Article type: Communication
Submitted: 27 Apr 2018
Accepted: 23 May 2018
First published: 29 May 2018

Download Citation

Chem. Commun., 2018,54, 6165-6168

Permissions

Request permissions

Enantioselective total synthesis of sagittacin E and related natural products

H. Abe, M. Fujimaki, E. Nakagawa, T. Kobayashi and H. Ito, Chem. Commun., 2018, 54, 6165 DOI: 10.1039/C8CC03438A

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.

Social activity

Fetching data from CrossRef.
This may take some time to load.

Chemical Communications

Enantioselective total synthesis of sagittacin E and related natural products†

Abstract

Supplementary files

Article information

Download Citation

Permissions

Enantioselective total synthesis of sagittacin E and related natural products

Social activity

Search articles by author

Spotlight

Advertisements