The Formal Total Synthesis of FR252921 – An Immunosuppressant

Abstract Image The Formal Total Synthesis of FR252921 – An Immunosuppressant European Journal of Organic Chemistry Volume 2013, Issue 2, pages 376–388, January 2013 J. S. Yadav and Sandip Sengupta Article first published online: 15 NOV 2012 | DOI: 10.1002/ejoc.201201097 Related topicshttp://onlinelibrary.wiley.com/doi/10.1002/ejoc.201201097/abstract   The formal total synthesis of FR252921 is described. The key steps include the preparation of three fragments starting from 1,4-butanediol, (R)-malic acid, and prenol, respectively, followed by two consecutive peptide couplings of the three fragments. AbstractClick on the mini-structures! The formal total synthesis of FR252921 is described. The key steps include the preparation of three fragments starting from 1,4-butanediol, (R)-malic acid, and prenol, respectively, followed by two consecutive peptide couplings of the three fragments. Other key steps involve an allene-type rearrangement or enyne isomerization to install the triene moiety, a Seebach methylation, a Julia olefination to construct the trisubstituted diene unit, and an enzymatic resolution strategy to generate the C-18 stereocenter. other articles of relevance

J Antibiot (Tokyo). 2003 Feb;56(2):62-7.

FR252921, a novel immunosuppressive agent isolated from Pseudomonas fluorescens no. 408813 II. In vitro property and mode of action.

Fujine KAbe F, Seki N, Ueda H, Hino M, Fujii T.

Source

Exploratory Research Laboratories, Fujisawa Pharmaceutical Co., Ltd., 5-2-3 Tokodai, Tsukuba, Ibaraki 300-2698, Japan. kiyotaga-fujine@po.fujisawa.co.jp

Abstract

A novel immunosuppressive agent, FR252921 was isolated from the cultured broth of a species of Pseudomonas fluorescens. We have shown that FR252921 inhibited splenic proliferation stimulated with LPS, insensitive to calcinuerin inhibitor. In this study, FR252921 was found to inhibit IL-2 and IL-12 production as well as proliferaion of splenocyte. Analysis of transcription activity revealed that FR252921 inhibited activating protein-1 (AP-1). Exposures of antigen presenting cells (APC) to FR252921 attenuated proliferation supplemented by naïve T cells. Further, FR252921 strongly suppressed splenic dendritic cell proliferation stimulated with LPS and anti-CD40 mAb, while it did not inhibit purified T cell activation, including CD154 expression and IL-2 production. These results suggest that APC is dominant target cell population.
Chemistry. 2009;15(14):3457-73. doi: 10.1002/chem.200802649.

Synthesis of two bioactive natural products: FR252921 and pseudotrienic acid B.

Amans D, Bellosta V, Cossy J.

Source

Laboratoire de Chimie Organique, ESPCI ParisTech, CNRS, 10 rue Vauquelin, 75231 Paris, France.

Abstract

Concise and highly convergent syntheses of the immunosuppressive agent FR252921 and the related antimicrobial natural product pseudotrienic acid B were achieved from a common intermediate by using optically active titanium complexes to control the configuration of the stereogenic centers, a highly stereo- and regioselective cross-metathesis to generate the triene moieties, and a Stille cross-coupling to install the dienic units.

Synthesis of a Promising Immunosuppressant:  FR252921

Dominique Amans , Véronique Bellosta , and Janine Cossy
Laboratoire de Chimie Organique, ESPCI, CNRS, 10 rue Vauquelin, 75231 Paris Cedex 05, France
Org. Lett., 2007, 9 (23), pp 4761–4764
DOI: 10.1021/ol702110k
Figure Links http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201201097/abstract   shark  

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