Issue 29, 2023

Synthesis of the spiroimine fragment of portimines A and B

Abstract

Portimines A and B are spirocyclic imine natural products, which display remarkable anticancer, anti-HIV, and antifouling activities. Herein, we report a facile synthesis of the spirocyclic core of portimines A and B. Our strategy utilized a scalable Diels–Alder addition of a 2-bromo-1,3-butadiene to a symmetrical malonate dienophile, coupled with a diastereoselective lactonization of the resulting malonate that enabled differentiation of the two carbonyl groups. This approach overcame issues encountered in previous studies focused on the use of exo selective Diels–Alder reactions, by programming formation of the key stereodiad of the spiroimine fragment into the diastereoselective lactonization event, rather than the cycloaddition step. Elaboration of the key lactone intermediate afforded a functionalized spirolactam fragment as a useful intermediate en route to the portimines. Importantly, a key alcohol intermediate could be resolved by enzymatic resolution, thereby providing an asymmetric route to the spiroimine fragment of portimines A and B.

Graphical abstract: Synthesis of the spiroimine fragment of portimines A and B

Supplementary files

Article information

Article type
Paper
Submitted
23 Jun 2023
Accepted
07 Jul 2023
First published
10 Jul 2023

Org. Biomol. Chem., 2023,21, 6008-6017

Synthesis of the spiroimine fragment of portimines A and B

X. Ding, A. Wung, D. P. Furkert and M. A. Brimble, Org. Biomol. Chem., 2023, 21, 6008 DOI: 10.1039/D3OB00998J

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