A Novel and Expeditious Approach to Unusual Spirolactam Building Blocks
- 1 May 2003
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 68 (11) , 4556-4559
- https://doi.org/10.1021/jo034023i
Abstract
A rapid access to 7-azaspiro[4.5]decan-6-ones 1 involving three regio- and chemoselective reactions starting from tetrabromonorbornyl derivatives is described. The alkaline H2O2 cleavage reaction of monosubstituted α-diketones 9 furnished the potential bridged bicyclic lactones 10 in a highly regio- and stereoselective manner. The radical-mediated, intermolecular bridgehead C−C bond formation of the versatile bridged lactones 10 with acrylonitrile followed by LAH reduction of the adduct 13 intriguingly leads to the formation of novel spirolactam building blocks 1.Keywords
This publication has 14 references indexed in Scilit:
- Spirolactams as Conformationally Restricted Pseudopeptides: Synthesis and Conformational AnalysisThe Journal of Organic Chemistry, 2002
- Construction of Azaspirocyclic Ketones through α-Hydroxyiminium Ion or α-Siloxy Epoxide Semipinacol RearrangementsOrganic Letters, 2001
- Two-directional synthesis. Part 1: A short formal synthesis of (±)-histrionicotoxin and (±)-histrionicotoxin 235ATetrahedron Letters, 2000
- 1,2,3,4-Tetrachloro-5,5-dimethoxy-cyclopenta-1,3-diene: Diels Alder Reactions and Applications of the Products FormedAdvanced Synthesis & Catalysis, 2000
- First Total Synthesis of the Marine Alkaloids (±)-Fasicularin and (±)-Lepadiformine Based on Stereocontrolled Intramolecular Acylnitroso-Diels−Alder ReactionJournal of the American Chemical Society, 2000
- Stereocontrolled synthesis of spirocyclicsTetrahedron, 1999
- Synthesis of (−)-Histrionicotoxin by a Tandem ProcessJournal of the American Chemical Society, 1999
- Asymmetric synthesis XV : enantiospecific synthesis of (+) and (−) isonitramines from a common chiral intermediateTetrahedron Letters, 1988
- Enantioselective Total Syntheses of Sibirine, Nitramine, and IsonitramineHETEROCYCLES, 1987
- A total synthesis of d,1-histrionicotoxinTetrahedron Letters, 1985