Formal Total Synthesis of Manzacidin B via Sequential Diastereodivergent Henry Reaction

• Araki, Yuya

• Miyoshi, Natsumi

• Morimoto, Kazuki

• Kudoh, Takayuki

• Mizoguchi, Haruki

• Sakakura, Akira

Abstract

A formal total synthesis of manzacidin B is described. beta,beta-Disubstituted gamma-hydroxy-beta-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.

Journal

• Journal of Organic Chemistry

  Journal of Organic Chemistry 85 (2), 798-805, 2019-12-18

  American Chemical Society

Keywords

• Organic Chemistry

Details

• CRID: 1050850578886821120
• NII Article ID: 120006948961
• NII Book ID: AA00704100
• ISSN: 00223263
• ISSN: 15206904
• DOI: 10.1021/acs.joc.9b02811
• Web Site: https://ousar.lib.okayama-u.ac.jp/58256
• Web Site: https://pubs.acs.org/doi/pdf/10.1021/acs.joc.9b02811
• Text Lang: en
• Article Type: journal article
• Data Source:
  • IRDB
  • Crossref
  • CiNii Articles
  • KAKEN