Use of cyclobutyl derivatives as intermediates in the synthesis of 1,2a,3,8b-tetrahydro-2H-cyclobuta[c]chromenes

Starting from cyclobutanones and tertiary cyclobutanols several new chromenes containing a cyclobutane ring have been prepared by acid catalyzed intramolecular alkylation of an oxygen-carrying aromatic ring. Interestingly one of the cyclobutanols leads to 3-[(4-methoxyphenoxy)methyl]-2,2,3-trimethyl...

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Bibliographic Details
Published inTetrahedron Vol. 60; no. 2; pp. 449 - 457
Main Authors Bernard, AM, Floris, C, Frongia, A, Piras, PP, Secci, F
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 05.01.2004
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
electrophilic aromatic substitutions
PALLADIUM
RING EXPANSION
ALKYLIDENECYCLOPROPANES
CATALYZED NUCLEOPHILIC-SUBSTITUTION
cyclopropanes
ring opening
kinetic resolution
OXASPIROPENTANES
capsorubin
cyclobutanones
STRAIN
GRIGNARD-REAGENTS
CYCLIZATION
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Summary:Starting from cyclobutanones and tertiary cyclobutanols several new chromenes containing a cyclobutane ring have been prepared by acid catalyzed intramolecular alkylation of an oxygen-carrying aromatic ring. Interestingly one of the cyclobutanols leads to 3-[(4-methoxyphenoxy)methyl]-2,2,3-trimethylcyclopentanone that is a precursor in the synthesis of the carotenoid pigment capsorubin. (C) 2003 Elsevier Ltd. All rights reserved.
ISSN:0040-4020
DOI:10.1016/j.tet.2003.11.018