Total synthesis of the macrolide antibiotic cytovaricin

Evans, David A.; Kaldor, Stephen W.; Jones, Todd K.; Clardy, Jon; Stout, Thomas J.

doi:10.1021/ja00175a038

Cited by 331 publications

(161 citation statements)

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“…3b. The configuration of the spiroketal in 2 was quite similar to that in cytovaricin [6], therefore, the structure of 2 was determined as that in Fig. 1.…”

mentioning

confidence: 99%

“…Ushikulides A (1) and B (2) are related to phthoramycin [8], kaimonolide A [9], and the aglycone of cytovaricin [6,10], which are thought to be members of the oligomycin family from the point of view of biosynthesis. Oligomycin F [11] and 41-demethylhomooligomycin B [12], which have a 26-membered lactone ring in their structures, are known to possess immunosuppressive activities.…”

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confidence: 99%

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Ushikulides A and B, Immunosuppressants Produced by a Strain of Streptomyces sp.

2005

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Novel immunosuppressants, ushikulides A and B, were isolated from the culture broth of Streptomyces sp. IUK-102. Ushikulides A and B both have the same molecular formula, determined as C 40 H 68 O 10 . The structures of both compounds were elucidated to be novel 22-membered macrolides. Both compounds showed immunosuppressive activity for murine splenocyte proliferation in vitro. Binding of each of these drug-protein complexes to a catalytic subunit of carcineurin causes inhibition of signal transduction in T cell activation [3]. However, these agents have some adverse side-effects such as nephrotoxicity and chronic rejection [4,5]. Another potent immunosuppressive agent is desired to develop a safer medical treatment. During our screening for immunosuppressants from microbial products, novel immunosuppressants ushikulides A (1) and B (2) were found in the culture broth of Streptomyces sp. IUK-102 (Fig. 1). This paper describes the isolation, structure elucidation, and biological activities of these compounds.The producing strain, Streptomyces sp. IUK-102, was isolated from a soil sample collected in Ibaraki prefecture, J. Antibiot. 58 (6)

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“…3b. The configuration of the spiroketal in 2 was quite similar to that in cytovaricin [6], therefore, the structure of 2 was determined as that in Fig. 1.…”

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confidence: 99%

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confidence: 99%

Ushikulides A and B, Immunosuppressants Produced by a Strain of Streptomyces sp.

2005

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“…After screening various possibilities, Amberlyst 15, an ion-exchange resin, 9) was found to be an effective acid catalyst. Treatment of 1 with several alcohols as solvents in the presence of this resin furnished the corresponding products (2, 6 and 7) in moderate yields (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

Structure-activity Relationship for FR901464: A Versatile Method for the Conversion and Preparation of Biologically Active Biotinylated Probes

Motoyoshi

Horigome

Ishigami

et al. 2004

Bioscience, Biotechnology, and Biochemistry

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“…The desired tetramer 13 was generated by treating 9 with the more robust silyl protecting group tert-butyldiphenylsilyl chloride 44 (TBDPSCl). Selective deprotection of the fully protected tetramer 13 is achieved by employing hydrogen fluoridepyridine 45 In theory, Novolacs can have 'ortho-ortho', 'ortho-para' and 'para-para' methylene bridges. A consequence of the different linking structures is that they dictate the free ortho or para position and, of course, the structure of the Novolac resin.…”

Section: Para-linked Compoundsmentioning

confidence: 99%