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Literature DB >> 23013246

Syntheses of papyracillic acids: application of the tandem chain extension-acylation reaction.

Abstract

A synthetic approach to the papyracillic acid family of natural products has been developed. The spiroacetal core is rapidly assembled through an unprecedented zinc carbenoid-mediated tandem chain extension-acylation reaction. Subsequent functional group manipulation provided access to papyracillic acid B and 4-epi-papyracillic acid C. The successful preparation of these molecules resulted in the clarification of structural assignments of members of this family of natural products.

Entities: Chemical Disease Species

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Year: 2012 PMID： 23013246 PMCID： PMC3477294 DOI： 10.1021/jo3017617

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

11 in total

1. Formal synthesis of (+)-brefeldin A: application of a zinc-mediated ring expansion reaction.

Authors: Weimin Lin; Charles K Zercher
Journal: J Org Chem Date: 2007-05-12 Impact factor: 4.354

2. The enzymic formation of penicillic acid.

Authors: K Axberg; S Gatenbeck
Journal: FEBS Lett Date: 1975-06-01 Impact factor: 4.124

3. Potential production and detoxification of penicillic acid in mold-fermented sausage (salami).

Authors: A Ciegler; H J Mintzlaff; D Weisleder; L Leistner
Journal: Appl Microbiol Date: 1972-07

4. Tandem chain extension-homoenolate formation: the formation of alpha-methylated-gamma-keto esters.

Authors: R Hilgenkamp; C K Zercher
Journal: Org Lett Date: 2001-09-20 Impact factor: 6.005

5. Tandem chain extension-aldol reaction: syn selectivity with a zinc enolate.

Authors: S Lai; C K Zercher; J P Jasinski; S N Reid; R J Staples
Journal: Org Lett Date: 2001-12-27 Impact factor: 6.005

6. Ring expansions of beta-keto lactones with zinc carbenoids: syntheses of (+)-patulolide A and (+/-)-patulolide B.

Authors: Matthew D Ronsheim; Charles K Zercher
Journal: J Org Chem Date: 2003-03-07 Impact factor: 4.354

7. Stereoselective formation of a functionalized dipeptide isostere by zinc carbenoid-mediated chain extension.

Authors: Weimin Lin; Cory R Theberge; Timothy J Henderson; Charles K Zercher; Jerry Jasinski; Ray J Butcher
Journal: J Org Chem Date: 2009-01-16 Impact factor: 4.354

8. Practical procedures for the preparation of N-tert-butyldimethylsilylhydrazones and their use in modified Wolff-Kishner reductions and in the synthesis of vinyl halides and gem-dihalides.

Authors: Michael E Furrow; Andrew G Myers
Journal: J Am Chem Soc Date: 2004-05-05 Impact factor: 15.419