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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Enantioselective total synthesis of the highly selective sphingosine-1-receptor VPC01091 by the Heck desymmetrization of a non-activated cyclopentene-fused spiro-pyrrolidinone

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Khan, Ismat Ullah ; Kattela, Shivashankar ; Hassan, Abbas ; Correia, Carlos Roque Duarte
Total Authors: 4
Document type: Journal article
Source: ORGANIC & BIOMOLECULAR CHEMISTRY; v. 14, n. 40, p. 9476-9480, OCT 28 2016.
Web of Science Citations: 14

A novel, efficient and enantioselective Heck-Matsuda desymmetrization of non-activated cyclopentene-fused spiro-pyrrolidinones was developed. The reaction provided the Heck products in good to excellent yields and selectivities and tolerated a variety of functional groups in arenediazonium tetrafluoroborates (12 examples) with respect to its electronics and substitution patterns. This methodology was successfully applied in the concise enantioselective total synthesis of VPC01091 (2b), a drug candidate for the treatment of multiple sclerosis. (AU)

FAPESP's process: 14/05407-4 - Strategies for the dessymmetrization of cyclopentene scaffolds using the enantioselective Heck-Matsuda reaction and their potential synthetic applications.
Grantee:Shivashankar Kattela
Support Opportunities: Scholarships in Brazil - Post-Doctorate
FAPESP's process: 14/25770-6 - New frontiers in cross-coupling reactions promoted by palladium: combining enantioselective catalysis, C-H activations, new materials and in flux reactions aiming at high efficiency and sustainability in synthetic processes
Grantee:Carlos Roque Duarte Correia
Support Opportunities: Research Projects - Thematic Grants
FAPESP's process: 13/07600-3 - CIBFar - Center for Innovation in Biodiversity and Drug Discovery
Grantee:Glaucius Oliva
Support Opportunities: Research Grants - Research, Innovation and Dissemination Centers - RIDC