Asymmetric synthesis of the four stereoisomers of 5-deoxystrigol

[Display omitted] Two approaches to the strigolactone tricyclic lactone skeleton 2 were investigated using ketene/ketene-iminium cycloaddition to olefins. Finally, the first enantioselective access to the four stereoisomers of 5-deoxystrigol 1 is reported using an intramolecular [2+2] cycloaddition...

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Bibliographic Details
Published inTetrahedron letters Vol. 55; no. 48; pp. 6577 - 6581
Main Authors Lachia, Mathilde, Dakas, Pierre-Yves, De Mesmaeker, Alain
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 26.11.2014
Elsevier
Subjects
[2+2] Cycloaddition
Chemistry
Chemistry, Organic
Cyclobutanone
Ketene/ketene-iminium
Physical Sciences
Science & Technology
Strigolactone
Total synthesis
[2+2] Cycloaddition
Ketene/ketene-iminium
Cyclobutanone
Strigolactone
Total synthesis
ACID
GERMINATION
INTRAMOLECULAR 2+2 CYCLOADDITION
PLANT HORMONES
INHIBITION
OLEFINS
VINYLKETENES
STRIGOLACTONES
STIMULANT
DERIVATIVES
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Summary:[Display omitted] Two approaches to the strigolactone tricyclic lactone skeleton 2 were investigated using ketene/ketene-iminium cycloaddition to olefins. Finally, the first enantioselective access to the four stereoisomers of 5-deoxystrigol 1 is reported using an intramolecular [2+2] cycloaddition of homochiral ketene-iminium salts 5. Very high asymmetric control was achieved with C-2 symmetric pyrrolidines as chiral auxiliary.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2014.10.040