226879-32-9Relevant academic research and scientific papers
Diastereoselective Synthesis of Highly Substituted Tetrahydrofurans by Pd-Catalyzed Tandem Oxidative Cyclization-Redox Relay Reactions Controlled by Intramolecular Hydrogen Bonding
Brooks, Joshua L.,Xu, Liping,Wiest, Olaf,Tan, Derek S.
, p. 57 - 75 (2017/04/26)
Palladium-catalyzed oxidative cyclization of alkenols provides a convenient entry into cyclic ethers but typically proceeds with little or no diastereoselectivity for cyclization of trisubstituted olefins to form tetrahydrofurans due to the similar energi
Synthesis of a lactone diastereomer of the cembranolide uprolide D
Marshall, James A.,Griot, Celine A.,Chobanian, Harry R.,Myers, William H.
supporting information; experimental part, p. 4328 - 4331 (2010/12/25)
Figure Presented. A convergent stereoselective synthesis of a C1/C14 bis-epimer of uprolide D is described in which an intramolecular Barbier-type reaction was employed for macrocyclization with concomitant introduction of the C1 and C14 stereocenters of a fused α-methylene lactone ring through an anti-Felkin-Anh transition state. Unlike previous examples of allyl chromium additions, none of the Felkin-Anh derived adduct could be detected.
Transannular Diels-Alder model studies on the total synthesis of chatancin. The furanophane approach. Part 1: Assembly of the acyclic substrates
Toro, Andras,Wang, Yuan,Deslongchamps, Pierre
, p. 2765 - 2768 (2007/10/03)
Synthesis of three generations of model substrates with advancing similarity to chatancin are presented. In the first two generations, an Ireland-Claisen based six-step sequence supplied the trans-dienophile to be connected by dithiane chemistry to furfurals. In the third generation, a homogeraniol based dienophile aldehyde was coupled with a dilithiated 3- furoic acid. Subsequently, all three generations were concluded with similar functional group modifications as a preparation for a malonate-furyl chloride based macrocyclization.
