Synthesis of a tetrabenzyl-substituted 10-membered cyclic diamide

Takayuki Doi, Hiroyuki Nagamiya, Masaya Kokubo, Kazunori Hirabayashi, Takashi Takahashi

Research output: Contribution to journalArticlepeer-review

19 Citations (Scopus)

Abstract

A conformationally constrained 10-membered cyclic diamide was designed and synthesized. Conformational analysis suggested that the 9-membered ring formation was preferred to the direct formation of 10-membered ring. On the basis of the prediction, lactonization of 9-membered lactone, followed by intramolecular ester-amide transformation afforded the desired 10-membered cyclic diamide.

Original languageEnglish
Pages (from-to)2957-2963
Number of pages7
JournalTetrahedron
Volume58
Issue number15
DOIs
Publication statusPublished - 2002 Apr 8
Externally publishedYes

Keywords

  • Amidation
  • Diamide
  • Ester-amide transformation

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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