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Translated title of the contribution: Stereoselective Synthesis of Dehydroamino Acids and Its Application to the Synthesis of Nitrogen-containing Natural Products

Yoko Yasuno, Hironori Okamura, Tetsuro Shinada

Research output: Contribution to journalArticlepeer-review

Abstract

Dehydroamino acids are often found in nitrogen-containing natural products and widely utilized as a useful intermediate for the synthesis of nitrogen-containing organic molecules. In this article, we would like to report our recent efforts toward development of the stereoselective syntheses of α,β -dehydroamino acids and its application to the synthesis of nitrogen containing natural products and biologically active molecules. We developed a new olefination reagent,(diphenylphosphono)glycine esters, which allowed smooth condensation with aldehydes to provide E-dehydroamino acids in a stereoselective manner. The new method was successfully applied to the stereoselective synthesis of dehydroisoleucine and the tripeptide side chain of phomopsin A. Stereoselective synthesis of (2S,6R)-diamino(- 5R,7)-dihydroxy-heptanoic acid, 2,6-diaminosuberic acid, and kaitocephalin via hydrogenation of dehydroamino acid moieties are also described.

Translated title of the contributionStereoselective Synthesis of Dehydroamino Acids and Its Application to the Synthesis of Nitrogen-containing Natural Products
Original languageJapanese
Pages (from-to)331-342
Number of pages12
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume80
Issue number4
DOIs
Publication statusPublished - 2022

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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