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

Ken ichi Takao; Yuki Kojima; Tomo Miyashita; Kentaro Yashiro; Tatsuya Yamada; Kin ichi Tadano

doi:10.3987/COM-08-S(F)11

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

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

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-review

9 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 language	English
Pages (from-to)	167-172
Number of pages	6
Journal	Heterocycles
Volume	77
Issue number	1
DOIs	https://doi.org/10.3987/COM-08-S(F)11
Publication status	Published - 2009 Jan 1

Keywords

Dieckmann Condensation
Guttiferae
Perforatumone
Sharpless Asymmetic Epoxidation

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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10.3987/COM-08-S(F)11

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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.",

keywords = "Dieckmann Condensation, Guttiferae, Perforatumone, Sharpless Asymmetic Epoxidation",

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T1 - Enantioselective synthesis of A 3,5,5-trialkylated tetronic acid derivative

AU - Takao, Ken ichi

AU - Kojima, Yuki

AU - Miyashita, Tomo

AU - Yashiro, Kentaro

AU - Yamada, Tatsuya

AU - Tadano, Kin ichi

PY - 2009/1/1

Y1 - 2009/1/1

N2 - 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.

AB - 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.

KW - Dieckmann Condensation

KW - Guttiferae

KW - Perforatumone

KW - Sharpless Asymmetic Epoxidation

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

Abstract

Keywords

ASJC Scopus subject areas

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