Issue 14, 2022

Total synthesis of huperserratines A and B

Abstract

Huperserratines A (1) and B (2), two novel macrocyclic Lycopodium alkaloids, possess an aza-12-membered ring. Here, we describe the first total synthesis of these two natural products in 12 steps. Key elements of the synthesis include the Suzuki–Miyaura coupling, the Hosomi–Sakurai reaction, ring-closing metathesis, dihydroxylation, and the Swern oxidation. A gram-scale ring-closing metathesis was pivotal in forging the challenging aza-12-membered ring. This total synthesis would enable future studies on the structure–activity relationship of 1 and 2.

Graphical abstract: Total synthesis of huperserratines A and B

Supplementary files

Article information

Article type
Research Article
Submitted
14 апр 2022
Accepted
20 май 2022
First published
24 май 2022

Org. Chem. Front., 2022,9, 3664-3668

Total synthesis of huperserratines A and B

Z. Deng, X. Wu, Z. Yuan, N. Yu, Y. Ou and Q. Zhao, Org. Chem. Front., 2022, 9, 3664 DOI: 10.1039/D2QO00608A

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