The synthesis of heliannuol C, an allelochemical from Helianthus annuus

The synthesis of the allelochemical heliannuol C 1 is described by employing a Bargellini condensation and a Claisen rearrangement to install the gem-dimethyl and vinyl functionalities, respectively. A Dieckmann cyclisation of diester 11 enabled the generation of the benzoxepane ring system enshrine...

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Bibliographic Details
Published in:Tetrahedron letters 2006-06, Vol.47 (24), p.4019-4021
Main Authors: Biswas, Bidyut, Sen, Prabir K., Venkateswaran, Ramanathapuram V.
Format: Article
Language:English
Subjects:
Allelochemical
Bargellini condensation
Benzoxepane ring system
Claisen orthoester rearrangement
Heliannuol C
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Summary:The synthesis of the allelochemical heliannuol C 1 is described by employing a Bargellini condensation and a Claisen rearrangement to install the gem-dimethyl and vinyl functionalities, respectively. A Dieckmann cyclisation of diester 11 enabled the generation of the benzoxepane ring system enshrined in 1.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2006.04.011