ArticleOrganic & biomolecular chemistry2018
Concise total synthesis of (+)-asperazine A and (+)-pestalazine B.
Article in Organic & biomolecular chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed.
- Total synthesis of complex 2,5-diketopiperazine alkaloids.The Alkaloids. Chemistry and biology · 2023Review
- Total Synthesis of the Proposed Structure of (-)-Novofumigatamide, Isomers Thereof, and Analogues. Part I.The Journal of organic chemistry · 2022Article
- Total synthesis of himastatin.Science (New York, N.Y.) · 2022Article
- Structure and Function of NzeB, a Versatile C-C and C-N Bond-Forming Diketopiperazine Dimerase.Journal of the American Chemical Society · 2020Article
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Authors and funding
4 authors.
Funding
Abstract
The highly convergent total synthesis of dimeric diketopiperazine alkaloids (+)-asperazine A and (+)-pestalazine B is described. A critical aspect of our expedient route was the development of a directed regio- and diastereoselective C3-N1' coupling of complex tetracyclic diketopiperazine components. This late-stage heterodimerization reaction was made possible by design of tetracyclic diketopiperazines that allow C3-carbocation coupling of the electrophilic component to the N1' locus of the nucleophilic fragment. The application of this new coupling reaction to the first total synthesis of (+)-asperazine A led to our revision of the sign and magnitude of the optical rotation for the reported structure.
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