Work

Exploiting Pseudo C2-Symmetry for an Efficient Synthesis of the F-Ring of the Spongistatins

Year: 2013

Type: article

Abstract: A concise and efficient synthesis of the F-ring fragment of the potent antimitotic marine macrolide spongistatin 1 has been developed. The key sequence involves double cross-metathesis/Sharpless asymmetric dihydroxylation reactions to establish four stereocenters in a pseudo C2-symmetric array, followed by a selective protection reaction that breaks the pseudosymmetry, establishes a fifth stereocenter, and effectively differentiates the ester termini. Overall, the six contiguous stereocenters in the C(37)-C(45) F-ring fragment are established in just seven steps.

Source: Organic Letters

DOI: 10.1021/ol402604s

Authors: Paul S. Tanis, Joshua R. Infantine, James L. Leighton

Institution: Columbia University

Language: English

Topic: Synthetic Organic Chemistry Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Awards: Asymmetric Synthesis of Marcolide Antibiotics, G4345430935, Efficient Synthesis of the Spongistatin EF Ring Segment and Analogue SAR Study