Stereocontrolled total synthesis of (--)-kaitocephalin.
This paper describes the successful implementation of a stereocontrolled strategy for the total chemical synthesis of the pyrrolidine-based alkaloid (--)-kaitocephalin. This scalable synthetic route profits from the strategic utilization of substrate-controlled manipulations for the iterative installation of the requisite stereogenic centers. The key transformations include a diastereoselective modified Claisen condensation, a chemo- and diastereoselective reduction of a beta-keto ester, and the substrate-directed hydrogenation of a dehydroamino ester derivative. During the course of our investigations, an interesting stereoconvergent cyclization reaction was discovered for the efficient assembly of the kaitocephalin 2,2,5-trisubstituted pyrrolidine core.
Vaswani
Rishi G
RG
Department of Chemistry, University of California-Irvine, Irvine, California 92697-2025, USA.
Chamberlin
A Richard
AR
D000215:Acylation; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008956:Models, Chemical; D010084:Oxidation-Reduction; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D011758:Pyrroles; C442421:kaitocephalin