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

2002; American Chemical Society; Volume: 4; Issue: 26 Linguagem: Inglês

10.1021/ol027074v

1523-7060

Matthew D. McReynolds, Kevin T. Sprott, Paul R. Hanson,

Click Chemistry and Applications

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.