Total synthesis of (-)-pestalotiopsin A

Kenichi Takao, Nobuhiko Hayakawa, Reo Yamada, Taro Yamaguchi, Urara Morita, Soujiro Kawasaki, Kin Ichi Tadano

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

(Chemical Equation Presented) A big "+": The total synthesis of (-)-pestalotiopsin A has been achieved, thereby establishing the absolute stereochemistry of natural (+)-pestalotiopsin A (see scheme). The synthesis features a [2+2] cycloaddition, an aldol reaction, and an intramolecular Nozaki-Hiyama-Kishi reaction to construct the (E)-cyclononene ring.

Original languageEnglish
Pages (from-to)3426-3429
Number of pages4
JournalAngewandte Chemie - International Edition
Volume47
Issue number18
DOIs
Publication statusPublished - 2008 Apr 21

Fingerprint

Stereochemistry
Cycloaddition
Cycloaddition Reaction
pestalotiopsin A
3-hydroxybutanal

Keywords

  • Chiral auxiliaries
  • Cyclization
  • Cycloaddition
  • Synthesis design

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Medicine(all)

Cite this

Takao, K., Hayakawa, N., Yamada, R., Yamaguchi, T., Morita, U., Kawasaki, S., & Tadano, K. I. (2008). Total synthesis of (-)-pestalotiopsin A. Angewandte Chemie - International Edition, 47(18), 3426-3429. https://doi.org/10.1002/anie.200800253

Total synthesis of (-)-pestalotiopsin A. / Takao, Kenichi; Hayakawa, Nobuhiko; Yamada, Reo; Yamaguchi, Taro; Morita, Urara; Kawasaki, Soujiro; Tadano, Kin Ichi.

In: Angewandte Chemie - International Edition, Vol. 47, No. 18, 21.04.2008, p. 3426-3429.

Research output: Contribution to journalArticle

Takao, K, Hayakawa, N, Yamada, R, Yamaguchi, T, Morita, U, Kawasaki, S & Tadano, KI 2008, 'Total synthesis of (-)-pestalotiopsin A', Angewandte Chemie - International Edition, vol. 47, no. 18, pp. 3426-3429. https://doi.org/10.1002/anie.200800253
Takao K, Hayakawa N, Yamada R, Yamaguchi T, Morita U, Kawasaki S et al. Total synthesis of (-)-pestalotiopsin A. Angewandte Chemie - International Edition. 2008 Apr 21;47(18):3426-3429. https://doi.org/10.1002/anie.200800253
Takao, Kenichi ; Hayakawa, Nobuhiko ; Yamada, Reo ; Yamaguchi, Taro ; Morita, Urara ; Kawasaki, Soujiro ; Tadano, Kin Ichi. / Total synthesis of (-)-pestalotiopsin A. In: Angewandte Chemie - International Edition. 2008 ; Vol. 47, No. 18. pp. 3426-3429.
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