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The synthesis of a novel benzodiazocine via an intramolecular Staudinger/aza-Wittig cyclization

✍ Scribed by Ian A O'Neil; Clare L Murray; Andrew J Potter; S.Barret Kalindjian


Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
117 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis


The novel pyrrolobenzodiazocine (1) has been prepared by an intramolecular Staudinger/aza Wittig protocol from the precursor azido aldehyde (2) in a remarkable 93% yield. Aldehyde (2) was prepared by coupling protected homoprolinol with 2-azidobenzoic acid followed by deprotection and oxidation.


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Novel N-acetyl C-aza-2-deoxy-D-ribonucleosides were synthesized from 2-deoxy-D-ribose via a consecutive procedure of the addition of ortho-lithiated pyrimidine salt, Staudinger-aza-Wittig ring cyclization, and reduction of cyclic imine.