Synthesis of (-)-sordarin

Shunsuke Chiba, Mitsuru Kitamura, Koichi Narasaka*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

96 Citations (Scopus)

Abstract

The first total synthesis of (-)-sordarin (1) was accomplished exploiting the following key reactions: (i) Ag(I)-catalyzed oxidative radical cyclization of a cyclopropanol derivative leading to a bicyclo-[5.3.0]decan-3-one skeleton; (ii) Pd(0)-catalyzed intramolecular allylation reaction resulting in the entire strained bicyclo[2.2.1]heptan-2-one framework of sordaricin (2); (iii) selective dihydroxylation of terminal alkenes by the combined use of OsO4 and PhB(OH)2; and (iv) β(1,2-cis)-selective glycosidation via a 1,3-anchimeric assistance from a 4-methoxybenzoyl group.

Original languageEnglish
Pages (from-to)6931-6937
Number of pages7
JournalJournal of the American Chemical Society
Volume128
Issue number21
DOIs
Publication statusPublished - May 31 2006
Externally publishedYes

ASJC Scopus Subject Areas

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry

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