Total synthesis of antibiotic streptothricin F

doi:10.1016/S0040-4039(00)87506-1

Tetrahedron Letters

Volume 23, Issue 29, 1982, Pages 2961-2964

https://doi.org/10.1016/S0040-4039(00)87506-1 Get rights and content

Abstract

The first total synthesis of streptothricin F was achieved and its structure was unequivocally confirmed.

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The STs inhibit protein biosynthesis in prokaryotic3 as well as eukaryotic cells, such as yeast,4–6 fungi,7 protozoa,8 insects,9 and plants.10 The chemical structures of STs were proposed in 196111,12 and were finally confirmed by the total synthesis of ST-F in 1982;13,14 the location of the carbamate moiety in d-gulosamine was assigned to C10 (Fig. 1A). A streptolidine lactam moiety is considered essential for the activity15,16 because ST-F acid (Fig. 1B), a ring-opened product of the streptolidine lactam in ST-F, did not exhibit antibacterial activity.
A synthesis of (2S,3R,4R)-3,4-dihydroxyarginine, a metabolic intermediate of streptothricin, was accomplished. The (3R,4R)-dihydroxy groups were constructed by asymmetric syn-dihydroxylation of (E)-alkene, which was obtained by cross-metathesis of allylamine and l-vinylglycine derivatives. The synthesis of (2S,3S,4S)-3,4-dihydroxyarginine was also achieved in the same manner. The (2S,3R,4R)-3,4-dihydroxyarginine exhibited inhibitory activity against inducible nitric oxide synthase, unlike (2S,3S,4S)-3,4-dihydroxyarginine.
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In addition to terrestrial sources, marine organisms have also proven to be a rich source of biologically active 1,2-diamines, including the anti-tuberculosis agent manadomanzamine A (15),28,29 the antineoplastic agent agelastatin A (12),30 and eudistomin-K sulfoxide (13),31 a representative member of the eudistomin family that displays activity against both RNA and DNA viruses.32 While a number of the alkaloids represented in Fig. 2 have succumbed to total synthesis, most recently pactamycin (14),33,34 others including manadomanzamine A (15), remain unassailed and, as such, offer unique challenges for the development of new diamination methods. Despite the recent progress in diamination methodology, many of these targets present significant challenges to direct alkene amination methods and, as such, are an impetus to the continued investigation of diamine methods that offer enantiocontrol, differential N-protection and, importantly in the context of such complex targets, functional group compatibility.
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The reaction of dimethyl (4S,5S)-1-benzyl-2-oxo-3-(9″-phenylfluoren-9″-yl)-imidazolidine-4,5-dicarboxylate (3) with several organolithium reagents afforded the corresponding enantiomerically pure monoketones (4a-e) in good to excellent yields. Chloromethyl-ketone 4b was ultimately transformed into ureido-amide 8 which incorporates the bicyclic core of streptolidine lactam (1), a component of the streptrothricin antibiotics.

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^☆: This work was presented at the 24th Symposium on the Chemistry of Natural Products, Osaka, October 1981.

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Total synthesis of antibiotic streptothricin F☆

Abstract

Carbohydr. Res.

Proc. Soc. Exp. Biol. Med.

Chem. Lett.