Total Synthesis of the Epimer at C-6′ of the Miharamycin B Framework

Abstract

The total synthesis of the epimer at C-6′ of the core of the complex nucleoside antibiotic miharamycin B is reported. Opti­mization of the N-glycosylation key step involving the atypical 2-aminopurine nucleobase and a bicyclic glycosyl donor enabled to access the N ⁹-nucleoside in reasonable yield which was further decorated. The stereochemistry at C-6′ has been secured by X-ray crystallography.

Key words

antibiotics - natural products - nucleosides - total synthesis

References and Notes

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9

Marcelo F., Silva, F. V. M.; Goulart, M.; Justino, J.; Blériot, Y.; Rauter, A. P. in preparation.

12

CCDC 716056 contains the supplementary crystallographic data for this structure. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via http://www.ccdc.ac.uk/data _request/cif.

13

Hydroxy esters 5 and 5′ were difficult to separate and therefore were used as a mixture.

14

CCDC 716057 contains the supplementary crystallographic data for this structure. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via http://www.ccdc.ac.uk/data _request/cif.

15

CCDC 695608 contains the supplementary crystallographic data for this structure. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via http://www.ccdc.ac.uk/data _request/cif.