Bioinspired Synthesis of Platensimycin from Natural ent-Kaurenoic Acids.

Abstract

The biomimetic formal synthesis of the antibiotic platensimycin for the treatment of infection by multidrug-resistant bacteria was accomplished starting from either ent-kaurenoic acid or grandiflorenic acid, each of which is a natural compound available in multigram scale from its natural source. Apart from the natural origin of the selected precursors, the keys of the described approach are the long-distance functionalization of ent-kaurenoic acid at C11 and the efficient protocol for the A-ring degradation of the diterpene framework.

• Authors: Álvaro Pérez, José F Quílez Del Moral, Alberto Galisteo, Juan M Amaro, Alejandro F Barrero
• Journal: Organic letters (Org Lett) Vol. 25 Issue 29 Pg. 5401-5405 (07 28 2023) ISSN: 1523-7052 [Electronic] United States
• PMID: 37338151 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• kaurenoic acid
• platensimycin
• Diterpenes
• Adamantane
• Aminobenzoates

Topics

• Diterpenes (metabolism)
• Adamantane
• Aminobenzoates