Synthetic application of acylnitroso Diels-Alder derived aminocyclopentenols: total synthesis of (+)-streptazolin.
Concise total syntheses of (+)-streptazolin 1 and its more stable dihydro derivative 2 were accomplished via an intramolecular aldol condensation strategy starting from readily available aminocyclopentenol (-)-7. The synthetic sequence included reductive amination, stereoselective epoxidation, intramolecular aldol (and condensation) reaction, and Wittig reaction. The overall yield for dihydro derivative 2 from aminocyclopentenol (-)-7 was about 7% for a total of 14 steps.
Li
Fangzheng
F
Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556, USA.
Warshakoon
Namal C
NC
Miller
Marvin J
MJ
D000215:Acylation; D003517:Cyclopentanes / Q000737:chemistry; D008968:Molecular Conformation; D009603:Nitroso Compounds / Q000737:chemistry*; D010880:Piperidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D003517:Cyclopentanes; D009603:Nitroso Compounds; D010880:Piperidines; C428165:streptazolin