Stereoselective route to oxetanocin carbocyclic analogues based on a [2 + 2] photocycloaddition to a chiral 2(5H)-furanone

Albert Rustullet; Ramon Alibés; Pedro De March; Marta Figueredo; Josep Font

doi:10.1021/ol0710616

Stereoselective route to oxetanocin carbocyclic analogues based on a [2 + 2] photocycloaddition to a chiral 2(5H)-furanone

Albert Rustullet, Ramon Alibés, Pedro De March, Marta Figueredo, Josep Font

Department of Chemistry

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

37 Citations (Scopus)

Abstract

The synthesis of the trisubstituted cyclobutane 7, which is a suitable precursor for the preparation of oxetanocin carbocyclic analogues, is described. The key step involves a regio- and diastereoselective [2 + 2] photochemical reaction of ketene diethyl acetal with (S)-5-pivaloyloxymethyl-2(5H)-furanone, 3. As an application of this methodology, (-)-cyclobut-A has been prepared from the intermediate 7. © 2007 American Chemical Society.

Original language	English
Pages (from-to)	2827-2830
Journal	Organic Letters
Volume	9
Issue number	15
DOIs	https://doi.org/10.1021/ol0710616
Publication status	Published - 19 Jul 2007

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title = "Stereoselective route to oxetanocin carbocyclic analogues based on a [2 + 2] photocycloaddition to a chiral 2(5H)-furanone",

abstract = "The synthesis of the trisubstituted cyclobutane 7, which is a suitable precursor for the preparation of oxetanocin carbocyclic analogues, is described. The key step involves a regio- and diastereoselective [2 + 2] photochemical reaction of ketene diethyl acetal with (S)-5-pivaloyloxymethyl-2(5H)-furanone, 3. As an application of this methodology, (-)-cyclobut-A has been prepared from the intermediate 7. {\textcopyright} 2007 American Chemical Society.",

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T1 - Stereoselective route to oxetanocin carbocyclic analogues based on a [2 + 2] photocycloaddition to a chiral 2(5H)-furanone

AU - Rustullet, Albert

AU - Alibés, Ramon

AU - De March, Pedro

AU - Figueredo, Marta

AU - Font, Josep

PY - 2007/7/19

Y1 - 2007/7/19

N2 - The synthesis of the trisubstituted cyclobutane 7, which is a suitable precursor for the preparation of oxetanocin carbocyclic analogues, is described. The key step involves a regio- and diastereoselective [2 + 2] photochemical reaction of ketene diethyl acetal with (S)-5-pivaloyloxymethyl-2(5H)-furanone, 3. As an application of this methodology, (-)-cyclobut-A has been prepared from the intermediate 7. © 2007 American Chemical Society.

AB - The synthesis of the trisubstituted cyclobutane 7, which is a suitable precursor for the preparation of oxetanocin carbocyclic analogues, is described. The key step involves a regio- and diastereoselective [2 + 2] photochemical reaction of ketene diethyl acetal with (S)-5-pivaloyloxymethyl-2(5H)-furanone, 3. As an application of this methodology, (-)-cyclobut-A has been prepared from the intermediate 7. © 2007 American Chemical Society.

U2 - 10.1021/ol0710616

DO - 10.1021/ol0710616

M3 - Article

VL - 9

SP - 2827

EP - 2830

IS - 15

ER -

Stereoselective route to oxetanocin carbocyclic analogues based on a [2 + 2] photocycloaddition to a chiral 2(5H)-furanone

Abstract

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