Short Synthesis of Skeletally and Stereochemically Diverse Small Molecules by Coupling Petasis Condensation Reactions to Cyclization Reactions

Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts, United States
Angewandte Chemie International Edition (Impact Factor: 11.26). 05/2006; 45(22):3635-8. DOI: 10.1002/anie.200600497
Source: PubMed


(Chemical Equation Presented) An efficient synthetic pathway to skeletally and stereochemically diverse molecules is described. Densely functionalized amino alcohols were readily synthesized through a Petasis three-component, boronic acid Mannich reaction. Their intramolecular cyclization provided a collection of diverse single-isomer compounds with 15 different types of skeletons in three to five steps.

2 Reads
  • Source
    [Show abstract] [Hide abstract]
    ABSTRACT: A branching synthetic strategy was used to efficiently generate structurally diverse scaffolds, which span a broad area of chemical descriptor space, and their biological activity against MRSA was demonstrated.
    Chemical Communications 09/2006; 37(31):3296-8. DOI:10.1039/b607710b · 6.83 Impact Factor
  • Source
    [Show abstract] [Hide abstract]
    ABSTRACT: The present essay offers an overview of the latest developments in the chemistry of organoboron compounds. The unique structural characteristics and the versatile reactivity profile of organoboron compounds continue to expand their roles in several areas of chemistry. A growing number of boron-mediated reactions have become vital tools for synthetic chemistry, particularly in asymmetric synthesis, metal-catalyzed processes, acid catalysis, and multicomponent reactions. As a result, boronic acids and related molecules have now evolved as major players in synthetic and medicinal chemistry. Moreover, their remnant electrophilic reactivity, even under physiological conditions, has allowed their incorporation in a growing number of bioactive molecules, including bortezomib, a clinically approved anticancer agent. Finally, the sensitive and selective binding of boronic acids to diols and carbohydrates has led to the development of a growing number of novel chemosensors for the detection, quantification, and imaging of glucose and other carbohydrates. There is no doubt that the chemistry of organoboron compounds will continue to expand into new discoveries and new applications in several fields of science.
    Australian Journal of Chemistry 01/2007; 60(11-11):795-798. DOI:10.1071/CH07360 · 1.56 Impact Factor
  • [Show abstract] [Hide abstract]
    ABSTRACT: Over the past decade, major advances in the preparation and utilization of organoboron reagents have been applied to virtually all areas of organic synthesis. The present review collates recent examples of the use of organoboron reagents in the synthesis of alpha-amino acids and their derivatives. Aryl- and alkenylboronic acids have been used in the asymmetric synthesis of a-amino acids through conjugate addition to unsaturated amino acids and the Petasis three-component coupling reaction. Additionally, alpha-amino acid derivatives with organoboron functionality on the side-chain have been prepared and used in metal-catalyzed cross-coupling reactions to prepare cross-linked amino acids and complex cyclic peptide natural products.
    Australian Journal of Chemistry 01/2007; 60(11-11):799-810. DOI:10.1071/CH07103 · 1.56 Impact Factor
Show more

Preview (2 Sources)

2 Reads
Available from