Total synthesis of xanthanolides

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

Research output: Contribution to journalArticle

37 Citations (Scopus)

Abstract

The total synthesis and determination of the absolute configuration of (+)- and (-)-sundiversifolide have been achieved via intramolecular acylation and Wittig-lactonization as the key steps. The xanthanolide sesquiterpene lactones, 8-epi-xanthatin (1), dihydroxanthatin (2), and xanthatin (3) were also prepared, starting from a common intermediate derived from the synthesis of sundiversifolide.

Original languageEnglish
Pages (from-to)8407-8419
Number of pages13
JournalTetrahedron
Volume66
Issue number43
DOIs
Publication statusPublished - Oct 23 2010

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Acylation
Sesquiterpenes
Lactones
xanthatin
sundiversifolide

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Matsuo, K., Ohtsuki, K., Yoshikawa, T., Shishido, K., Yokotani-Tomita, K., & Shindo, M. (2010). Total synthesis of xanthanolides. Tetrahedron, 66(43), 8407-8419. https://doi.org/10.1016/j.tet.2010.08.061

Total synthesis of xanthanolides. / Matsuo, Kazumasa; Ohtsuki, Keiko; Yoshikawa, Takashi; Shishido, Kozo; Yokotani-Tomita, Kaori; Shindo, Mitsuru.

In: Tetrahedron, Vol. 66, No. 43, 23.10.2010, p. 8407-8419.

Research output: Contribution to journalArticle

Matsuo, K, Ohtsuki, K, Yoshikawa, T, Shishido, K, Yokotani-Tomita, K & Shindo, M 2010, 'Total synthesis of xanthanolides', Tetrahedron, vol. 66, no. 43, pp. 8407-8419. https://doi.org/10.1016/j.tet.2010.08.061
Matsuo K, Ohtsuki K, Yoshikawa T, Shishido K, Yokotani-Tomita K, Shindo M. Total synthesis of xanthanolides. Tetrahedron. 2010 Oct 23;66(43):8407-8419. https://doi.org/10.1016/j.tet.2010.08.061
Matsuo, Kazumasa ; Ohtsuki, Keiko ; Yoshikawa, Takashi ; Shishido, Kozo ; Yokotani-Tomita, Kaori ; Shindo, Mitsuru. / Total synthesis of xanthanolides. In: Tetrahedron. 2010 ; Vol. 66, No. 43. pp. 8407-8419.
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