Synthesis of trans-fused [5,5] bicyclic lactones/lactams as templates for serine protease inhibition

Efficient routes have been developed for the synthesis of the trans-lactone 2, the trans-lactam 3 and their 3-substituted analogues based upon cyclisation strategies using Mukaiyama's reagent. 3β-Allyl, thiophenyl and propyl lactones 5 inhibit chymotrypsin and human leucocyte elastase and are r...

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Bibliographic Details
Published in:	Tetrahedron letters Vol. 39; no. 38; pp. 6979 - 6982
Main Authors:	Kelly, Henry A., Bolton, Richard, Brown, Stuart A., Coote, Steven J., Dowle, Mike, Dyer, Ulrich, Finch, Harry, Golding, Doreen, Lowdon, Andrew, McLaren, Jessica, Montana, John G., Owen, Martin R., Pegg, Neil A., Ross, Barry C., Thomas, Rhian, Walker, Dawn A.
Format:	Journal Article
Language:	English
Published:	Elsevier Ltd 17-09-1998
Subjects:	nonfood plant products
Online Access:	Get full text
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Summary:	Efficient routes have been developed for the synthesis of the trans-lactone 2, the trans-lactam 3 and their 3-substituted analogues based upon cyclisation strategies using Mukaiyama's reagent. 3β-Allyl, thiophenyl and propyl lactones 5 inhibit chymotrypsin and human leucocyte elastase and are representative of a novel class of serine protease inhibitors. Efficient routes to trans-lactone 1, the novel trans-lactam 2 and their 3-substituted derivatives are described, providing access to novel classes of serine protease inhibitors.
ISSN:	0040-4039 1873-3581
DOI:	10.1016/S0040-4039(98)01481-6