An architectonic macrolide library based on a C2-symmetric macrodiolide toward pharmaceutical compositions

Hayato Nakano, Akihiro Sugawara, Tomoyasu Hirose, Hiroaki Gouda, Shuichi Hirono, Satoshi Omura, Toshiaki Sunazuka

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

Abstract A stereodivergent approach to creation of a specific 14-membered macrolide library is described. We designed a new 14-membered macrolide template possessing 10 sterogenic centers, and established a new library of fully-synthesized 14-membered ring compounds. The designed macrodiolides were synthesized through a convergent approach using an Evans aldol reaction, Keck esterification, and Yamaguchi macrolactonization, or Mitsunobu macrolactonization, as key steps. Moreover, introduction of an aminosugar to a macrodiolide aglycone by Schmidt glycosylation also afforded a new macrodiolide. Comparison between the conformation analysis of the macrolides, which we designed, and NMR analysis of the synthetic macrolides, indicated our stereoisomer library has significant diversity.

Original languageEnglish
Article number26353
Pages (from-to)6569-6579
Number of pages11
JournalTetrahedron
Volume71
Issue number37
DOIs
Publication statusPublished - 2015 Dec 4
Externally publishedYes

Keywords

  • Erythromycin A
  • Macrodiolides
  • Macrolactonization
  • Natural product-inspired compounds
  • Stereochemical diversity

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'An architectonic macrolide library based on a C2-symmetric macrodiolide toward pharmaceutical compositions'. Together they form a unique fingerprint.

Cite this