Total Synthesis and Biological Evaluation of Cell Adhesion Inhibitors Peribysin A and B: Structural Revision of Peribysin B

Kalmode, Hanuman P. ; Handore, Kishor L. ; Rajput, Raveena ; Shaikh, Samir R. ; Gonnade, Rajesh G. ; Kulkarni, Kiran A. ; Reddy, D. Srinivasa (2018) Total Synthesis and Biological Evaluation of Cell Adhesion Inhibitors Peribysin A and B: Structural Revision of Peribysin B Organic Letters, 20 (22). pp. 7003-7006. ISSN 1523-7060

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Official URL: http://doi.org/10.1021/acs.orglett.8b02838

Related URL: http://dx.doi.org/10.1021/acs.orglett.8b02838

Abstract

Total synthesis of potent cell-adhesion inhibitors peribysins A and B has been accomplished for the first time in racemic form. A Diels–Alder/aldol sequence to build the skeleton and decoration of the desired functionalities of the targeted natural products using highly stereoselective operations are the highlights. The structures of synthesized peribysins were fully characterized using spectral data and single-crystal X-ray analysis. Through this total synthesis, the initially proposed structure of peribysin B has been revised. Furthermore, the cell-adhesion inhibition potential of the scaffold (two peribysins + three analogues) was confirmed using anti-adhesion assay.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society
ID Code:121850
Deposited On:22 Jul 2021 14:36
Last Modified:22 Jul 2021 14:36

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