Total synthesis of auripyrones A and B and determination of the absolute configuration of auripyrone B

Ichiro Hayakawa, Takuma Takemura, Emi Fukasawa, Yuta Ebihara, Natsuki Sato, Takayasu Nakamura, Kiyotake Suenaga, Hideo Kigoshi

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

(Figure Presented) The winner takes it aldol: The total synthesis of auripyrones A and B was achieved using a diastereoselective aldol-type reaction with 2, 6-diethyl-3, 5-dimethyl-4-pyrone as a key step. The stereostructure and absolute configura-tion of auripyrone B has also been determined.

Original languageEnglish
Pages (from-to)2401-2405
Number of pages5
JournalAngewandte Chemie - International Edition
Volume49
Issue number13
Publication statusPublished - 2010 Mar 22

Fingerprint

Pyrones
auripyrone B
3-hydroxybutanal
auripyrone A

Keywords

  • Aldol reactions
  • Auripyrones
  • Diastereoselectivity
  • Natural products
  • Total synthesis

ASJC Scopus subject areas

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

Cite this

Hayakawa, I., Takemura, T., Fukasawa, E., Ebihara, Y., Sato, N., Nakamura, T., ... Kigoshi, H. (2010). Total synthesis of auripyrones A and B and determination of the absolute configuration of auripyrone B. Angewandte Chemie - International Edition, 49(13), 2401-2405.

Total synthesis of auripyrones A and B and determination of the absolute configuration of auripyrone B. / Hayakawa, Ichiro; Takemura, Takuma; Fukasawa, Emi; Ebihara, Yuta; Sato, Natsuki; Nakamura, Takayasu; Suenaga, Kiyotake; Kigoshi, Hideo.

In: Angewandte Chemie - International Edition, Vol. 49, No. 13, 22.03.2010, p. 2401-2405.

Research output: Contribution to journalArticle

Hayakawa, I, Takemura, T, Fukasawa, E, Ebihara, Y, Sato, N, Nakamura, T, Suenaga, K & Kigoshi, H 2010, 'Total synthesis of auripyrones A and B and determination of the absolute configuration of auripyrone B', Angewandte Chemie - International Edition, vol. 49, no. 13, pp. 2401-2405.
Hayakawa I, Takemura T, Fukasawa E, Ebihara Y, Sato N, Nakamura T et al. Total synthesis of auripyrones A and B and determination of the absolute configuration of auripyrone B. Angewandte Chemie - International Edition. 2010 Mar 22;49(13):2401-2405.
Hayakawa, Ichiro ; Takemura, Takuma ; Fukasawa, Emi ; Ebihara, Yuta ; Sato, Natsuki ; Nakamura, Takayasu ; Suenaga, Kiyotake ; Kigoshi, Hideo. / Total synthesis of auripyrones A and B and determination of the absolute configuration of auripyrone B. In: Angewandte Chemie - International Edition. 2010 ; Vol. 49, No. 13. pp. 2401-2405.
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