Work

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

Year: 2024

Type: article

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 macrocyclic 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 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 macrocyclic bridges.

Source: Tetrahedron Letters

DOI: 10.1016/j.tetlet.2024.155184

Authors: Jesus M. Madrigal Lombera, Ian B. Seiple

Institution: University of California, San Francisco

Language: English

Topic: Organic Chemistry Synthesis Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze

Funders: National Science Foundation, National Institutes of Health, University of California, San Francisco, National Institute of General Medical Sciences

Awards: G3792000654, Modular synthesis of antibiotic and anticancer classes of natural products