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Updated: Jan 22, 2026

Synthesis and Characterization of Functionalized Metal-organic Frameworks
Published on: September 5, 2014
Stereoselective Synthesis of the C1-C22 Carbon Framework of (-)-Amphidinolide K
Somnath S Chandankar1,2, Sadagopan Raghavan1,2
1Department of Organic Synthesis & Process Chemistry , Indian Institute of Chemical Technology , Hyderabad 500007 , India.
Abstract:
Two stereoselective routes to the C7-C22 subunit of amphidinolide K are disclosed. Jacobsen's hydrolytic kinetic resolution and Sharpless' asymmetric dihydroxylation reactions have been employed for the construction of the tetrahydrofuran ring. The C10-C11, C16-C17, C9-O, and C18-O bonds have been created using α-chloro sulfide intermediates and [2,3] sigmatropic rearrangement. Marshall's propargylation protocol is utilized to create the C4 stereogenic center, and regioselective hydrozirconation/iodine quench afforded an alkenyl iodide which is employed in the NHK coupling with the C7-C22 subunit. Oxonia-Cope rearrangement resulted in the creation of the C18 carbinol stereogenic center and chain elongation.
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