A Concise Route to Structurally Diverse DMP 323 Analogues via Highly Functionalized 1,4-Diamines

The utility of functionalized 1,4-diamines, produced via a temporary phosphorus tether (P-tether)/ring-closing metathesis (RCM)/hydrolysis sequence, is demonstrated in the synthesis of structurally diverse DMP 323 analogues. These 1,4-diamines are transformed into various seven-membered heterocycles...

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Bibliographic Details
Published in:Organic letters 2002-12, Vol.4 (26), p.4673-4676
Main Authors: McReynolds, Matthew D, Sprott, Kevin T, Hanson, Paul R
Format: Article
Language:English
Subjects:
Alcohols
Diamines - chemistry
Heterocyclic Compounds - chemical synthesis
HIV Protease Inhibitors - chemical synthesis
Urea - analogs & derivatives
Urea - chemical synthesis
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Summary:The utility of functionalized 1,4-diamines, produced via a temporary phosphorus tether (P-tether)/ring-closing metathesis (RCM)/hydrolysis sequence, is demonstrated in the synthesis of structurally diverse DMP 323 analogues. These 1,4-diamines are transformed into various seven-membered heterocycles via insertion of the appropriate nuclei “X”. Subsequent derivatization generates heterocyclic diols that are similar in structure to DMP 323, a notable member of a class of highly potent inhibitors of HIV protease.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol027074v