Total synthesis of (+)- and (-)-sundiversifolide via intramolecular acylation and determination of the absolute configuration

Keiko Ohtsuki, Kazumasa Matsuo, Takashi Yoshikawa, Chihiro Moriya, Kaori Tomita-Yokotani, Kozo Shishido, Mitsuru Shindo

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

Intramolecular acylation of an organolithium leads to an efficient stereocontrolled total synthesis of both enantiomers of sundiversifolide. The absolute configuration was determined by HPLC analysis and allelopathy assay. The y-lactone moiety resulted from a butenolide was obtained by the condensation of a bicyclic a-hydroxyhemiacetal with Ph3P=CMe(CO2R).

Original languageEnglish
Pages (from-to)1247-1250
Number of pages4
JournalOrganic Letters
Volume10
Issue number6
DOIs
Publication statusPublished - Mar 20 2008

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Allelopathy
acylation
Acylation
Enantiomers
enantiomers
Lactones
Condensation
Assays
condensation
High Pressure Liquid Chromatography
synthesis
configurations
butenolide
sundiversifolide

All Science Journal Classification (ASJC) codes

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry
  • Molecular Medicine

Cite this

Total synthesis of (+)- and (-)-sundiversifolide via intramolecular acylation and determination of the absolute configuration. / Ohtsuki, Keiko; Matsuo, Kazumasa; Yoshikawa, Takashi; Moriya, Chihiro; Tomita-Yokotani, Kaori; Shishido, Kozo; Shindo, Mitsuru.

In: Organic Letters, Vol. 10, No. 6, 20.03.2008, p. 1247-1250.

Research output: Contribution to journalArticle

Ohtsuki, Keiko ; Matsuo, Kazumasa ; Yoshikawa, Takashi ; Moriya, Chihiro ; Tomita-Yokotani, Kaori ; Shishido, Kozo ; Shindo, Mitsuru. / Total synthesis of (+)- and (-)-sundiversifolide via intramolecular acylation and determination of the absolute configuration. In: Organic Letters. 2008 ; Vol. 10, No. 6. pp. 1247-1250.
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