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Metal-free [3 + 2 + 1]/[2 + 2 + 1] Biscyclization: Stereospecific Construction with Concomitant Functionalization of Indolizin-5(1H)-one

Overview
Journal J Org Chem
Specialty Chemistry
Date 2013 Oct 31
PMID 24168348
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Abstract

A metal-free [3 + 2 + 1]/[2 + 2 + 1] biscyclization strategy has been developed for the stereospecific construction with concomitant derivation of biologically significant indolizin-5(1H)-ones from simple and commercial starting materials. The transformations are notable because they can yield five new σ bonds and six stereocenters including a quaternary carbon center in a single operation.

References
1.
Haffner C, Diaz C, Miller A, Reid R, Madauss K, Hassell A . Pyrrolidinyl pyridone and pyrazinone analogues as potent inhibitors of prolyl oligopeptidase (POP). Bioorg Med Chem Lett. 2008; 18(15):4360-3. DOI: 10.1016/j.bmcl.2008.06.067. View

2.
Santos V, Regasini L, Nogueira C, Passerini G, Martinez I, Bolzani V . Antiprotozoal sesquiterpene pyridine alkaloids from Maytenus ilicifolia. J Nat Prod. 2012; 75(5):991-5. DOI: 10.1021/np300077r. View

3.
Tietze L . Domino Reactions in Organic Synthesis. Chem Rev. 1996; 96(1):115-136. DOI: 10.1021/cr950027e. View

4.
Marigo M, Schulte T, Franzen J, Anker Jorgensen K . Asymmetric multicomponent domino reactions and highly enantioselective conjugated addition of thiols to alpha,beta-unsaturated aldehydes. J Am Chem Soc. 2005; 127(45):15710-1. DOI: 10.1021/ja055291w. View

5.
Alcaide B, Almendros P, Redondo M, Ruiz M . Diastereoselectivity enhancement in the 1,3-cycloaddition of beta-lactam aldehydes. Application to the synthesis of enantiopure indolizidinone amino esters. J Org Chem. 2005; 70(22):8890-4. DOI: 10.1021/jo051402y. View