Formal Total Synthesis of Manzacidin B via Sequential Diastereodivergent Henry Reaction

Yuya Araki, Natsumi Miyoshi, Kazuki Morimoto, Takayuki Kudoh, Haruki Mizoguchi, Akira Sakakura

Research output: Contribution to journalArticle

Abstract

A formal total synthesis of manzacidin B is described. β,β-Disubstituted γ-hydroxy-β-aminoalcohol, the key structure of manzacidin B, is stereoselectively constructed via sequential Henry reactions. By taking advantage of noncovalent interactions, such as intramolecular hydrogen bonding and chelation, we could diastereodivergently control the stereoselectivity of the Henry reaction.

Original languageEnglish
Pages (from-to)798-805
Number of pages8
JournalJournal of Organic Chemistry
Volume85
Issue number2
DOIs
Publication statusPublished - Jan 17 2020

ASJC Scopus subject areas

  • Organic Chemistry

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