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 Apr 2022
Accepted
20 Mai 2022
First published
24 Mai 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

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