Total synthesis of exigurin: the Ugi reaction in a hypothetical biosynthesis of natural products?
Organic & Biomolecular Chemistry Pub Date: 2019-12-11 DOI: 10.1039/C9OB02249J
Abstract
The first total synthesis of a marine natural product, exigurin, has been accomplished in 13 steps starting from (+)-menthone. The key intermediate (?)-10-epi-axisonitrile-3 was prepared by stereoselective intramolecular cyclopropanation followed by a cyclopropane ring opening reaction by the azide anion. The bioinspired Ugi reaction of (?)-10-epi-axisonitrile-3, formaldehyde, sarcosine and methanol successfully constructed the target exigurin in which its terpene and amino acid units were linked through an amide bond.
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Journal Name：Organic & Biomolecular Chemistry
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CAS no.: 89640-58-4
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