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- Title
Syntheses and Preliminary Biological Evaluations of the Dibromopyrrole‐Containing Marine Natural Products Agesasine A, Agesasine B, Longamide E and Various Congeners.
- Authors
Chen, Chengzhi; Yuan, Tingting; Lan, Ping; White, Lorenzo V.; Chen, Jing; Banwell, Martin G.
- Abstract
Total syntheses of the title marine natural products have been achieved and so confirming the structures originally assigned to them. Upon subjecting agesasine A and its corresponding ethyl ester to Mitsunobu conditions, a 1,5‐cyclodehydration reaction takes place to give 2‐oxazolines. In contrast, on subjecting agesasine B to the same Mitsunobu conditions, a simple dehydration reaction occurs to give the corresponding acrylate. A total synthesis of longamide E was achieved by engaging a 1,2‐disubstituted pyrrole in a lactam‐forming reaction and this was followed by a two‐fold and fully regio‐controlled bromination reaction. A distinctly different and possibly biomimetic route was used to synthesize, via the open‐chain natural product nakamurine B, longamide B and its methyl ester. Preliminary biological evaluations of the title alkaloids and various analogues against a small human cancer cell line panel reveals cytotoxic properties that vary significantly with structure.
- Subjects
MARINE natural products; BIOSYNTHESIS; DEHYDRATION reactions; METHYL formate; NATURAL products; ETHYL esters; LACTAMS
- Publication
European Journal of Organic Chemistry, 2023, Vol 26, Issue 16, p1
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.202300003