Efficient synthesis of (±)-de-O-methyllasiodiplodin

17 July 2024, Version 2
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Resorcinolic macrolides are a large class of fungal natural products with conserved resorcinolic ester cores within highly variable ten- to fourteen-membered macrocycles. They exhibit a broad range of biological activities, depending largely on the size and substitution on the macrocycle bridge. Here, we report a protecting group-free synthesis of (±)-de-O-methyllasiodiplodin, a minimal resorcinolic macrolide derived from the fungus Lasiodiplodia theobromae. The route proceeds in 42% yield over 5 steps (longest linear sequence) from 9-decenoic acid, a cheap and abundant starting material. Given the broad commercial availability of a variety of similar (terminal)-enoic acids, this route provides an entry to libraries of resorcinolic macrolides with highly variable macrocycle bridges.

Keywords

total synthesis
protecting group-free synthesis
polyketides
radicicol
hypothemycin
resorcinolic macrolides

Supplementary materials

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Description
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Supporting Information
Description
Procedures for synthesis and characterization of intermediates and final products.
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