Towards a [4+2] Route to ( )-decarestrictines J and H: Synthesis of a Bicyclic Key-intermediate
Sopa Chewchanwuttiwong [a], Arnaud Martel [b], Duang Buddhasukh [a], Eric Brown [b], Florian Gallie* Author for corresponding; e-mail address: Gilles.Dujardin@univ_lemans.fr
Volume: Vol.31 No.2 May 2004
Short Communication
DOI:
Received: 14 October 2003, Revised: -, Accepted: 25 Febuary 2004, Published: -
Citation: Chewchanwuttiwong S., Martel A., Buddhasukh D., Brown E. and Gallie F., Towards a [4+2] Route to ( )-decarestrictines J and H: Synthesis of a Bicyclic Key-intermediate, Chiang Mai Journal of Science, 2004; 31(2): 181-184.
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.