Issue 30, 2023
From the journal:

Organic & Biomolecular Chemistry

Concise syntheses of (−)-habiterpenol and (+)-2,3-epi-habiterpenol via redox radical cyclization of alkenylsilane†

Haruki Taguchi,a   Mayuko Kawaguchi,a   Tohru Nagamitsu*a  and  Masaki Ohtawa ORCID logo *a  

* Corresponding authors

a Laboratory of Synthetic Natural Products Chemistry and Medicinal Research Laboratories, School of Pharmacy, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan
E-mail: ohtawam@pharm.kitasato-u.ac.jp, nagamitsut@pharm.kitasato-u.ac.jp

Abstract

The concise syntheses of (−)-habiterpenol and (+)-2,3-epi-habiterpenol from (3aR)-(+)-sclareolide and 6-methoxyindanone in 11 and 12 steps, respectively, were enabled by the regioselective addition of the TMS-indenyl anion and the facile stereoselective metal hydride hydrogen atom transfer (MHAT)-initiated redox radical cyclization of alkenylsilane.

Graphical abstract: Concise syntheses of (−)-habiterpenol and (+)-2,3-epi-habiterpenol via redox radical cyclization of alkenylsilane

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/D3OB01062G
Article type
Communication
Submitted
04 Jul 2023
Accepted
13 Jul 2023
First published
15 Jul 2023

Org. Biomol. Chem., 2023,21, 6129-6133

Permissions

Request permissions

Concise syntheses of (−)-habiterpenol and (+)-2,3-epi-habiterpenol via redox radical cyclization of alkenylsilane

H. Taguchi, M. Kawaguchi, T. Nagamitsu and M. Ohtawa, Org. Biomol. Chem., 2023, 21, 6129 DOI: 10.1039/D3OB01062G

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