Easy Access to 5-Alkyl-4-bromo-2(5H)-furanones: Synthesis of a Fimbrolide, an Acetoxyfimbrolide, and Bromobeckerelide

Pedro De March; Josep Font; Antonio Gracia; Zheng Qingying

doi:10.1021/jo00111a045

Easy Access to 5-Alkyl-4-bromo-2(5H)-furanones: Synthesis of a Fimbrolide, an Acetoxyfimbrolide, and Bromobeckerelide

Pedro De March, Josep Font, Antonio Gracia, Zheng Qingying

Departament de Química

Producció científica: Contribució a revista › Article › Recerca › Avaluat per experts

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Resum

Treatment of y-monosubstituted allenic esters with iV-bromosuccinimide in water yields 5-alkyl-4-bromo-2(5.H)-furanones, that can be transformed into 5-alkylidene-4-bromo-2(5H)-furanones in good overall yields. Starting with a simple allenic ester these transformations have been applied to a new synthesis of fimbrolide (la), acetoxyfimbrolide (lc), and bromobeckerelide (2a). © 1995, American Chemical Society. All rights reserved.

Idioma original	Anglès
Pàgines (de-a)	1814-1822
Revista	Journal of Organic Chemistry
Volum	60
Número	6
DOIs	https://doi.org/10.1021/jo00111a045
Estat de la publicació	Publicada - 1 de març 1995

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10.1021/jo00111a045

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@article{f8b3c0138bd14fa5afa2c5e5cf45a767,

title = "Easy Access to 5-Alkyl-4-bromo-2(5H)-furanones: Synthesis of a Fimbrolide, an Acetoxyfimbrolide, and Bromobeckerelide",

abstract = "Treatment of y-monosubstituted allenic esters with iV-bromosuccinimide in water yields 5-alkyl-4-bromo-2(5.H)-furanones, that can be transformed into 5-alkylidene-4-bromo-2(5H)-furanones in good overall yields. Starting with a simple allenic ester these transformations have been applied to a new synthesis of fimbrolide (la), acetoxyfimbrolide (lc), and bromobeckerelide (2a). {\textcopyright} 1995, American Chemical Society. All rights reserved.",

author = "{De March}, Pedro and Josep Font and Antonio Gracia and Zheng Qingying",

year = "1995",

month = mar,

day = "1",

doi = "10.1021/jo00111a045",

language = "English",

volume = "60",

pages = "1814--1822",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "6",

}

TY - JOUR

T1 - Easy Access to 5-Alkyl-4-bromo-2(5H)-furanones: Synthesis of a Fimbrolide, an Acetoxyfimbrolide, and Bromobeckerelide

AU - De March, Pedro

AU - Font, Josep

AU - Gracia, Antonio

AU - Qingying, Zheng

PY - 1995/3/1

Y1 - 1995/3/1

N2 - Treatment of y-monosubstituted allenic esters with iV-bromosuccinimide in water yields 5-alkyl-4-bromo-2(5.H)-furanones, that can be transformed into 5-alkylidene-4-bromo-2(5H)-furanones in good overall yields. Starting with a simple allenic ester these transformations have been applied to a new synthesis of fimbrolide (la), acetoxyfimbrolide (lc), and bromobeckerelide (2a). © 1995, American Chemical Society. All rights reserved.

AB - Treatment of y-monosubstituted allenic esters with iV-bromosuccinimide in water yields 5-alkyl-4-bromo-2(5.H)-furanones, that can be transformed into 5-alkylidene-4-bromo-2(5H)-furanones in good overall yields. Starting with a simple allenic ester these transformations have been applied to a new synthesis of fimbrolide (la), acetoxyfimbrolide (lc), and bromobeckerelide (2a). © 1995, American Chemical Society. All rights reserved.

U2 - 10.1021/jo00111a045

DO - 10.1021/jo00111a045

M3 - Article

SN - 0022-3263

VL - 60

SP - 1814

EP - 1822

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 6

ER -

Easy Access to 5-Alkyl-4-bromo-2(5H)-furanones: Synthesis of a Fimbrolide, an Acetoxyfimbrolide, and Bromobeckerelide

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