The Mitomyein Antibiotics. Synthetic Studies. V.¹ Preparation of 7-Methoxymitosene

Nucleophilic Nitrenoids Through π‐Acid Catalysis: Providing a Common Basis for Rapid Access into Diverse Nitrogen Heterocycles

“…The utility of the 2,3-dihydro-1 H-pyrrolizine synthesis was demonstrated by its application in the formal synthesis of 7methoxymitosene,w hichi sa ccessible in eight steps from the product of catalysis 27 (Scheme 10). [17,18] The reactivity of 2-alkynylaryl azide derivatives 29 under gold catalysis was independently reported in close conjunction by the groups of Gagosz and Zhang. [19] Both groups demonstrated how this approachp rovides rapid access to highly useful indole derivatives.…”

Mitomycinoid Alkaloids: Mechanism of Action, Biosynthesis, Total Syntheses, and Synthetic Approaches

“…In this manner, the bridged bicyclic adduct 261 was obtained in good yield and subsequently rearranged to the mitosene 262 by treatment with catalytic hydrochloric acid. After a series of six steps the authors intercepted a known [255] intermediate which was elaborated to 7-methoxymitosene 263 in two further steps.…”

Deoxyribonucleic Acid Damage by Monofunctional Mitomycins and Its Repair in Escherichia coli

“…Although MTC forms cross-links between complementary strands of DNA, the majority of mitomycin residues attach to DNA by a monofunctional alkylation in which one antibiotic molecule is attached to a single base (27), and nothing is known about the action of mitomycin residues attached monofunctionally to one strand of DNA. For the purpose of understanding the repair mechanism of crosslinked DNA on the one hand, and of understanding the action of mitomycin residues attached to DNA by a monofunctional alkylation on the other, 7-methoxymitosene 1,2,11) and decarbamoyl mitomycin C (DCMTC; 12), which have been assumed to act as a monofunctional alkylating agent (24), were used in this study. We present evidence that they produce DNA damage which results in the production of DNA strand breaks.…”