Diastereoselective Synthesis of the Aminocyclitol Core of Jogyamycin via an Allene Aziridination Strategy

Oxidative allene amination provides rapid access to densely functionalized amine-containing stereotriads through highly reactive bicyclic methylene­aziridine intermediates. This strategy has been demonstrated as a viable approach for the construction of the densely functionalized aminocyclitol core...

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Bibliographic Details
Published in:Organic letters 2016-01, Vol.18 (2), p.284-287
Main Authors: Gerstner, Nels C, Adams, Christopher S, Grigg, R. David, Tretbar, Maik, Rigoli, Jared W, Schomaker, Jennifer M
Format: Article
Language:English
Subjects:
Alkadienes - chemistry
Amination
Amines - chemistry
Molecular Structure
Oxidation-Reduction
Pactamycin - analogs & derivatives
Pactamycin - chemical synthesis
Pactamycin - chemistry
Pactamycin - pharmacology
Stereoisomerism
Streptomyces - chemistry
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Summary:Oxidative allene amination provides rapid access to densely functionalized amine-containing stereotriads through highly reactive bicyclic methylene­aziridine intermediates. This strategy has been demonstrated as a viable approach for the construction of the densely functionalized aminocyclitol core of jogyamycin, a natural product with potent antiprotozoal activity. Importantly, the flexibility of oxidative allene amination will enable the syntheses of modified aminocyclitol analogues of the jogyamycin core.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b03453