Photochemical cycloaddition of mono-, 1,1-, and 1,2-disubstituted olefins to a chiral 2(5H)-furanone. Diastereoselective synthesis of (+)-lineatin

Marta Racamonde; Ramon Alibés; Marta Figueredo; Josep Font; Pedro De March

doi:10.1021/jo800970u

Photochemical cycloaddition of mono-, 1,1-, and 1,2-disubstituted olefins to a chiral 2(5H)-furanone. Diastereoselective synthesis of (+)-lineatin

Marta Racamonde, Ramon Alibés, Marta Figueredo, Josep Font, Pedro De March

Department of Chemistry

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

24 Citations (Scopus)

Abstract

(Chemical Equation Presented) The photochemical [2 + 2] cycloaddition of (S)-4-methyl-5-O-pivaloyloxymethyl-2(5H)-furanone, 5, to vinyl acetate, vinyl pivalate, tert-butyl vinyl ether, 1,1-diethoxyethylene, and (Z)- and (E)-1,2-dichloroethylene has been studied. A practical synthesis of (+)-lineatin from 5 has been developed via the functionalized cyclobutane 6. © 2008 American Chemical Society.

Original language	English
Pages (from-to)	5944-5952
Journal	Journal of Organic Chemistry
Volume	73
Issue number	15
DOIs	https://doi.org/10.1021/jo800970u
Publication status	Published - 1 Aug 2008

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title = "Photochemical cycloaddition of mono-, 1,1-, and 1,2-disubstituted olefins to a chiral 2(5H)-furanone. Diastereoselective synthesis of (+)-lineatin",

abstract = "(Chemical Equation Presented) The photochemical [2 + 2] cycloaddition of (S)-4-methyl-5-O-pivaloyloxymethyl-2(5H)-furanone, 5, to vinyl acetate, vinyl pivalate, tert-butyl vinyl ether, 1,1-diethoxyethylene, and (Z)- and (E)-1,2-dichloroethylene has been studied. A practical synthesis of (+)-lineatin from 5 has been developed via the functionalized cyclobutane 6. {\textcopyright} 2008 American Chemical Society.",

author = "Marta Racamonde and Ramon Alib{\'e}s and Marta Figueredo and Josep Font and {De March}, Pedro",

year = "2008",

month = aug,

day = "1",

doi = "10.1021/jo800970u",

language = "English",

volume = "73",

pages = "5944--5952",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Photochemical cycloaddition of mono-, 1,1-, and 1,2-disubstituted olefins to a chiral 2(5H)-furanone. Diastereoselective synthesis of (+)-lineatin

AU - Racamonde, Marta

AU - Alibés, Ramon

AU - Figueredo, Marta

AU - Font, Josep

AU - De March, Pedro

PY - 2008/8/1

Y1 - 2008/8/1

N2 - (Chemical Equation Presented) The photochemical [2 + 2] cycloaddition of (S)-4-methyl-5-O-pivaloyloxymethyl-2(5H)-furanone, 5, to vinyl acetate, vinyl pivalate, tert-butyl vinyl ether, 1,1-diethoxyethylene, and (Z)- and (E)-1,2-dichloroethylene has been studied. A practical synthesis of (+)-lineatin from 5 has been developed via the functionalized cyclobutane 6. © 2008 American Chemical Society.

AB - (Chemical Equation Presented) The photochemical [2 + 2] cycloaddition of (S)-4-methyl-5-O-pivaloyloxymethyl-2(5H)-furanone, 5, to vinyl acetate, vinyl pivalate, tert-butyl vinyl ether, 1,1-diethoxyethylene, and (Z)- and (E)-1,2-dichloroethylene has been studied. A practical synthesis of (+)-lineatin from 5 has been developed via the functionalized cyclobutane 6. © 2008 American Chemical Society.

U2 - 10.1021/jo800970u

DO - 10.1021/jo800970u

M3 - Article

SN - 0022-3263

VL - 73

SP - 5944

EP - 5952

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 15

ER -

Photochemical cycloaddition of mono-, 1,1-, and 1,2-disubstituted olefins to a chiral 2(5H)-furanone. Diastereoselective synthesis of (+)-lineatin

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