Issue 30, 2019

Total synthesis of (+)-ar-macrocarpene

Abstract

This report features the first catalytic asymmetric total synthesis of a sesquiterpene, (+)-ar-macrocarpene (1), in 7 steps with 42.1% overall yields from commercially available inexpensive 5,5-dimethylcyclohexane 1,3-dione. This strategy relies on a key [3,3]-sigmatropic rearrangement effecting reductive transposition through allylic diazene rearrangement (ADR) in a single step from intermediate allylic alcohol (+)-12 under the Mitsunobu reaction conditions with o-nitrobenzenesulfonyl hydrazide (o-NBSH). Enantioselective reduction of α-bromo vinylogous ester 16 under the Corey–Bakshi–Shibata reduction conditions forges the required stereocenter in the allylic alcohol (+)-12 in a highly enantioenriched manner (95% ee).

Graphical abstract: Total synthesis of (+)-ar-macrocarpene

Supplementary files

Article information

Article type
Communication
Submitted
18 ဇွန် 2019
Accepted
09 ဇူ 2019
First published
09 ဇူ 2019

Org. Biomol. Chem., 2019,17, 7140-7143

Total synthesis of (+)-ar-macrocarpene

A. Khatua, S. Niyogi and V. Bisai, Org. Biomol. Chem., 2019, 17, 7140 DOI: 10.1039/C9OB01373C

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