Issue 3, 2025

Total synthesis of (–)-rhynchine A, (+)-rhynchine C and (+)-rhynchine E

Abstract

The first enantioselective total synthesis of (–)-rhynchine A, (+)-rhynchine C and (+)-rhynchine E has been successfully achieved in 11 steps via a convergent strategy. This efficient synthetic strategy provides 54 mg, 81 mg and 539 mg quantities of the above natural products at once, respectively, and revolves around three crucial transformations: firstly, substrate-controlled stereoselective ethylation and Michael addition are employed for the swift synthesis of the chiral proline fragment. Secondly, a mild Friedel–Crafts acylation is utilized for the formation of the tetracyclic skeleton. Lastly, a one-pot hydroxymethylation/oxidative cyclization method is employed for the construction of the tetrahydrofuran ring.

Graphical abstract: Total synthesis of (–)-rhynchine A, (+)-rhynchine C and (+)-rhynchine E

Supplementary files

Article information

Article type
Research Article
Submitted
22 Oct 2024
Accepted
29 Nov 2024
First published
30 Nov 2024

Org. Chem. Front., 2025,12, 824-828

Total synthesis of (–)-rhynchine A, (+)-rhynchine C and (+)-rhynchine E

Y. Cao, X. Lu, Y. Li, L. Huang and B. Gao, Org. Chem. Front., 2025, 12, 824 DOI: 10.1039/D4QO01987C

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