Enantioselective synthesis of A 3,5,5-trialkylated tetronic acid derivative

Kenichi Takao, Yuki Kojima, Tomo Miyashita, Kentaro Yashiro, Tatsuya Yamada, Kin ichi Tadano

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

A convenient and enantioselective method for the synthesis of 3,5,5-trialkylated tetronic acid has been developed. The Dieckmann-type condensation of enantioenriched α-acyloxy-α,α-dialkylated acetic acid ester (11) proceeded in the presence of lithium hexamethyldisilazide, providing the expected tetronic acid derivative (12) after quenching with methoxymethyl chloride. The product (12) was converted into a doubly prenylated tetronic acid derivative (13), which constitutes a substructure of perforatumone, a newly isolated polycyclic polyprenylated acylphloroglucinol-type natural product.

Original languageEnglish
Pages (from-to)167-172
Number of pages6
JournalHeterocycles
Volume77
Issue number1
DOIs
Publication statusPublished - 2009 Jan 1

Fingerprint

Derivatives
Biological Products
Chlorides
Condensation
Quenching
Acetates
tetronic acid
lithium hexamethyldisilazide
perforatumone

Keywords

  • Dieckmann Condensation
  • Guttiferae
  • Perforatumone
  • Sharpless Asymmetic Epoxidation

ASJC Scopus subject areas

  • Analytical Chemistry
  • Organic Chemistry
  • Pharmacology

Cite this

Takao, K., Kojima, Y., Miyashita, T., Yashiro, K., Yamada, T., & Tadano, K. I. (2009). Enantioselective synthesis of A 3,5,5-trialkylated tetronic acid derivative. Heterocycles, 77(1), 167-172. https://doi.org/10.3987/COM-08-S(F)11

Enantioselective synthesis of A 3,5,5-trialkylated tetronic acid derivative. / Takao, Kenichi; Kojima, Yuki; Miyashita, Tomo; Yashiro, Kentaro; Yamada, Tatsuya; Tadano, Kin ichi.

In: Heterocycles, Vol. 77, No. 1, 01.01.2009, p. 167-172.

Research output: Contribution to journalArticle

Takao, K, Kojima, Y, Miyashita, T, Yashiro, K, Yamada, T & Tadano, KI 2009, 'Enantioselective synthesis of A 3,5,5-trialkylated tetronic acid derivative', Heterocycles, vol. 77, no. 1, pp. 167-172. https://doi.org/10.3987/COM-08-S(F)11
Takao, Kenichi ; Kojima, Yuki ; Miyashita, Tomo ; Yashiro, Kentaro ; Yamada, Tatsuya ; Tadano, Kin ichi. / Enantioselective synthesis of A 3,5,5-trialkylated tetronic acid derivative. In: Heterocycles. 2009 ; Vol. 77, No. 1. pp. 167-172.
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