Issue 22, 2024

Asymmetric total synthesis of humulane sesquiterpenoids alashanoids B, C, E, and F and 2,9-humuladien-6-ol-8-one

Abstract

Naturally occurring sesquiterpenes having humulane frameworks are structurally intriguing and possess significant biological profiles. Asymmetric synthesis of the alashanoids B, C, E, and F and 2,9-humuladien-6-ol-8-one is achieved for the first time through a linear synthetic strategy. Intramolecular late-stage Nozaki–Hiyama–Kishi (NHK) coupling is employed to access the eleven-membered macrocyclic core present in the target molecules. The NHK precursors are accessed using the Evans and non-Evans syn and anti-aldol reaction as a key transformation. X-ray and ECD analysis reconfirmed the synthesized compounds’ structures and chirotopical properties.

Graphical abstract: Asymmetric total synthesis of humulane sesquiterpenoids alashanoids B, C, E, and F and 2,9-humuladien-6-ol-8-one

Supplementary files

Transparent peer review

To support increased transparency, we offer authors the option to publish the peer review history alongside their article.

View this article’s peer review history

Article information

Article type
Paper
Submitted
10 Mar 2024
Accepted
04 Apr 2024
First published
10 Apr 2024

Org. Biomol. Chem., 2024,22, 4478-4487

Asymmetric total synthesis of humulane sesquiterpenoids alashanoids B, C, E, and F and 2,9-humuladien-6-ol-8-one

R. Barik and S. Nanda, Org. Biomol. Chem., 2024, 22, 4478 DOI: 10.1039/D4OB00393D

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