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. 2024 Jul 15;63(29):e202314800.
doi: 10.1002/anie.202314800. Epub 2024 Jun 17.

Scalable Total Synthesis of Acremolactone B

Mengyu Ba  1   2 , Fengqi He  1   2 , Lu Ren  2 , William G Whittingham  3 , Peng Yang  1 , Ang Li  1   2
Affiliations

Scalable Total Synthesis of Acremolactone B

Mengyu Ba et al. Angew Chem Int Ed Engl. .

Abstract

Acremolactone B is a pyridine-containing azaphilone-type polyketide. The first total synthesis of this molecule was achieved on a gram scale, based on an aza-6π electrocyclization-aromatization strategy for construction of the tetra-substituted pyridine ring. A bicyclic intermediate was expeditiously prepared by using [2+2] photocycloaddition and chemoselective Baeyer-Villiger oxidation, which was further elaborated to a densely substituted aza-triene. An electrocyclization-aromatization cascade was utilized to forge the tetracyclic core of this natural product, and the side chain was introduced through diastereoselective acylation and reduction.

Keywords: Aza-6π Electrocyclization; Azaphilones; Natural Products; Pyridines; Total Synthesis.

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