Combinatorial synthesis of the 1,5-polyol system based on cross metathesis: Structure revision of amphidinol 3

Tohru Oishi, Mitsunori Kanemoto, Respati Swasono, Nobuaki Matsumori, Michio Murata

Research output: Contribution to journalArticle

47 Citations (Scopus)

Abstract

(Chemical Equation Presented) Combinatorial synthesis of a 1,5-polyol system corresponding to the C1-C14 unit of amphidinol 3 (AM3) and its diastereomers was achieved via chemoselective cross metathesis as the key step. Comparison of 13C NMR data of the synthetic specimens with that of AM3 led to a controversy regarding the originally proposed structure. From GC-MS analysis of the degradation product, the absolute configuration at C2 of AM3 has been revised to be R.

Original languageEnglish
Pages (from-to)5203-5206
Number of pages4
JournalOrganic Letters
Volume10
Issue number22
DOIs
Publication statusPublished - Dec 1 2008
Externally publishedYes

Fingerprint

metathesis
degradation
nuclear magnetic resonance
synthesis
products
configurations
Nuclear magnetic resonance
Degradation
polyol
amphidinol 3

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Combinatorial synthesis of the 1,5-polyol system based on cross metathesis : Structure revision of amphidinol 3. / Oishi, Tohru; Kanemoto, Mitsunori; Swasono, Respati; Matsumori, Nobuaki; Murata, Michio.

In: Organic Letters, Vol. 10, No. 22, 01.12.2008, p. 5203-5206.

Research output: Contribution to journalArticle

Oishi, Tohru ; Kanemoto, Mitsunori ; Swasono, Respati ; Matsumori, Nobuaki ; Murata, Michio. / Combinatorial synthesis of the 1,5-polyol system based on cross metathesis : Structure revision of amphidinol 3. In: Organic Letters. 2008 ; Vol. 10, No. 22. pp. 5203-5206.
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