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The development of strategies for construction of the aziridine core of the antitumor agents azinomycins A and B

โœ Scribed by Robert S. Coleman; Andrew J. Carpenter

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
780 KB
Volume
53
Category
Article
ISSN
0040-4020

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โœฆ Synopsis

The synthesis of the C6-C 13 aziridino [ 1,2a]pyrrolidine core substructure of the antitumor agents azinomycins A (la) and B (lb) is described. Key synthetic steps included Wadsworth-Horner-Emmons olefination for formation of the C7-C8 double bond, an E-selective electrophilic bromination of the C8 position, and a stereospecific intramolecular addition-elimination reaction sequence for formation of the N-C8 pyrrolidine bond.

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ChemInform Abstract: The Development of
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โœ R. S. COLEMAN; A. J. CARPENTER ๐Ÿ“‚ Article ๐Ÿ“… 2010 ๐Ÿ› John Wiley and Sons โš– 33 KB ๐Ÿ‘ 2 views

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Stereocontrolled Synthesis of the Fully Elaborated Aziridine Core of the Azinomycins. -The aziridino[1,2-a]pyrrolidine substructure of the antitumor agents Azinomycin A and B, isolated from Streptomyces griseofuscus, is synthesized from the key aldehyde (IV), which is obtained from (I) in 8 steps a