The First Total Synthesis of Various Thiostrepton-type Macrocyclic Antibiotics and the Structure-Bioactivity Relationship.

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Recently, many thiostrepton-type macrocyclic antibiotics, such as micrococcin P and P_1, and GE 2270 A, have been isolated from various secondary metabolites of Buchillus pumilus and Planobispola rose, respectively. The natural products exhibit very interesting bioactivities, such as antitumor and antibacterial activities, and include a characteristic main structure, in common 2,3,6-tristhiazolyl-substituted pyridine skeleton called Fragment A-C constructed of a polythiazole pyridine segment [Fragment A] and thiazolyl side chain called Fragment C. Furthermore, a unique polysubstitutedthiazole segment called Fragment B as a substructure. The total syntheses of the above mentioned antibiotics have been already accomplished by us. Here, similarly to the cases of the micrococcins P, P_1 and GE 2270 A, the first total synthesis of thiocilline I and convenient synthesis of the Fragment B-C of sulfomycin I, isolated from Bucillus bodius and Streptomyces viridchromogenes MCRL-0368 respectively, have been also achieved, after syntheses of he each Fragments A, B, and C, and then fragment condensations. These results will certainly contribute to the total synthesis of other similar thiostrepton-type antibiotics.