Total Syntheses of the Structures Assigned to Denigrins A, B, C, F, and G, 3,4-Diaryl-Pyrrole and -Pyrrolidinone Alkaloids, and the Conversion of Congener B into the Co-metabolite Spirodactylone

Liangguang Yi; Shen Tan; Lorenzo V White; Min-Yi Liang; Martin G Banwell

doi:10.1021/acs.jnatprod.3c01177

Total Syntheses of the Structures Assigned to Denigrins A, B, C, F, and G, 3,4-Diaryl-Pyrrole and -Pyrrolidinone Alkaloids, and the Conversion of Congener B into the Co-metabolite Spirodactylone

J Nat Prod. 2024 May 16. doi: 10.1021/acs.jnatprod.3c01177. Online ahead of print.

Authors

Liangguang Yi^{1

2

3}, Shen Tan^{1

2

3}, Lorenzo V White^{1

2

3}, Min-Yi Liang^{1

2

3}, Martin G Banwell^{1

2

3}

Affiliations

¹ Institute for Advanced and Applied Chemical Synthesis, College of Pharmacy, Jinan University, Guangzhou, Guangdong, 510632 China.
² State Key Laboratory of Bioactive Molecules and Druggability Assessment, Jinan University, Guangzhou, 510632, China.
³ Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM & New Drugs Research, Jinan University, Guangzhou, 510632, China.

PMID: 38754059
DOI: 10.1021/acs.jnatprod.3c01177

Abstract

The title marine natural products have been prepared by total synthesis and in the case of congeners 3, 6, and 7 for the first time. Each of these was obtained by manipulation of readily prepared denigrin B (2). The structure, 3, assigned to denigrin C is shown to be incorrect. Reaction of compound 2 with DDQ has led, in high yield, to the related natural product spirodactylone (16), while treating the corresponding permethyl ether 15 with PIFA/BF₃·Et₂O provides compound 20, embodying an isomeric framework.