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Synthesis of a conformationally locked version of puromycin amino nucleoside
Yongseok Choi1, Clifford George, Peter Strazewski
1Laboratory of Medicinal Chemistry, Center for Cancer Research, NCI, Frederick, Maryland 21702, USA.
Abstract:
[reaction: see text] A conformationally locked carbocyclic version of puromycin amino nucleoside was synthesized via Mitsunobu coupling of a 3-azido-substituted carbocyclic moiety with 6-chloropurine without interference from the azido group reacting with triphenylphosphine. The requisite 3-azido-substituted carbocyclic pseudosugar was prepared by a double inversion of configuration at C3' (nucleoside numbering) involving a nucleophilic displacement with azide.
