Diastereoselective synthesis of the 19-epi-C 18-C 25 segment of (-)-lasonolide a and an unusual inversion at C 19

Tomoyuki Yoshimura, Toshikazu Bando, Mitsuru Shindo, Kozo Shishido

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Diastereoselective construction of the 19-epi-C 18-C 25 segment of (-)-lasonolide A was achieved using a 5-exo-trigonal mode of radical cyclization for the creation of the contiguous quaternary and tertiary stereogenic centers at C 22 and C 23 as the key reaction step. During the dehydration stage, it was found that an unusual inversion of configuration took place.

Original languageEnglish
Pages (from-to)9241-9244
Number of pages4
JournalTetrahedron Letters
Volume45
Issue number50
DOIs
Publication statusPublished - Dec 6 2004
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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