651731-89-4Relevant academic research and scientific papers
Enantioselective Preparation of the C1-C11 Fragment of Apoptolidin
Paquette, William D.,Taylor, Richard E.
, p. 103 - 106 (2004)
(Equation presented) A novel approach toward the synthesis of the triene portion of the biologically active polyketide apoptolidin is described. The use of an iterative thionyl chloride rearrangement/oxidation sequence to construct trisubstituted olefins
Study of the total synthesis of (-)-exiguolide
Cook, Cyril,Liron, Frederic,Guinchard, Xavier,Roulland, Emmanuel
experimental part, p. 6728 - 6742 (2012/09/21)
In this article, we disclose the various routes and strategies we had to explore before finally achieving the total synthesis of (-)-exiguolide ((-)-1). Two first types of approaches were set, both relying on the Trost's domino ene-yne coupling/oxa-Michael reaction that we choose for its ability to control the geometry of the methylacrylate-bearing tetrahydropyrane ring B. In our first approach, we expected to assemble the two main fragments (C14-C21 and C1-C13) by creating the C13-C14 bond through a palladium(0)-catalyzed cross-coupling, but this step failed, unfortunately. In the second approach, which was more linear, we created the C16-C17 bond through condensation of a lithium acetylide on a Weinreb amide, and we assembled the C1-C5 and C6-C21 subunits through Trost's domino ene-yne coupling/oxa-Michael reaction. These two approaches served us to design an ameliorated third strategy, which finally led to the total synthesis of (-)-exiguolide.
