Studies on streptothricins VII. Determination of the ninhydrin-positive fragments of streptothricin antibiotics

Summary 1. A method for the quantitative analysis of the hydrolyzates of streptothricin antibiotics has been developed and has been used to determine the composition of representatives of the six types of this group of substances.2. The empirical formulae previously established for the new antibiotics have been confirmed and a proposed structure of the six types of streptothricins is discussed.3. On the basis of the results obtained, the hypothesis put forward that the empirical and structural formula of the antibiotic streptoline proposed by American workers is incorrect. A new empirical formula is proposed for this compound.Khimiya Prirodnykh Soedinenii, Vol. 1, No. 2, pp. 117–122, 1965     

Total synthesis of antibiotic streptothricin F

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

Synthesis of macrolide antibiotics.

Conclusions A stereodirected synthesis of the C¹-C₆- and C¹-C⁸-fragments of erythronolides A and B was carried out.For previous communication, see [1].Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 158–165, January, 1989.     

The convergent total synthesis and antibacterial profile of the natural product streptothricin F

A convergent, diversity-enabling total synthesis of the natural product streptothricin F has been achieved. Herein, we describe the potent antimicrobial activity of streptothricin F and highlight the importance of a total synthesis that allows for the installation of practical divergent steps for medicinal chemistry exploits. Key features of our synthesis include a Burgess reagent-mediated 1,2-anti-diamine installation, diastereoselective azidation of a lactam enolate, and a mercury(ii) chloride-mediated desulfurization-guanidination. The development of this chemistry enables the synthesis and structure–activity studies of streptothricin F analogs.

The second ever total synthesis of streptothricin F and the first achieved through a diversity-enabling convergent route. The synthesis is achieved in 35 total steps, with a longest linear sequence of 19 steps, and 0.40% overall yield.