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Towards a [4+2] Route to ()-decarestrictines J and H: Synthesis of a Bicyclic Key-intermediate


Paper Type 
Short Communication
Title 
Towards a [4+2] Route to ()-decarestrictines J and H: Synthesis of a Bicyclic Key-intermediate
Author 
Sopa Chewchanwuttiwong [a], Arnaud Martel [b], Duang Buddhasukh [a], Eric Brown [b], Florian Gallie
Email 
Gilles.Dujardin@univ_lemans.fr
Abstract:
We describe here the development of an approach to the synthesis of 3-oxo-7-hydroxy-9-decanolides of biological interest. This strategy involves two key steps : the inverse electron demand Hetero-Diels-Alder reaction of an original dienophile (1,5-dimethoxy-cyclohexa-1,4-diene), which will ensure the construction of an advanced structure in a very short number of steps, and the ring opening of a functionalized bicyclic lactol, leading to the requisite decanolide. The diastereocontrolled synthesis of such a lactol will be detailed in this communication.
Start & End Page 
181 - 184
Received Date 
2003-10-14
Revised Date 
Accepted Date 
2004-02-25
Full Text 
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Keyword 
cycloaddition, decarestrictine, Tin(IV) chloride, 9-decanolide
Volume 
Vol.31 No.2 May 2004
DOI 
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