Stereoselective total synthesis of (+)-streptazolin by using a temporary silicon-tethered RCM strategy.
A stereoselective total synthesis of (+)-streptazolin 1 was accomplished starting from readily available aminocyclopentenol (-)-7. The synthetic sequence highlights an intramolecular aldol condensation strategy to construct the piperidine core and a silicon-tethered ring-closing metathesis strategy to install the Z exocyclic ethylidene side chain of streptazolin. Separate protodesilylation and Tamao oxidation of a common intermediate 32 afforded streptazolin and the precursor for 13-hydroxystreptazolin. The overall yield for (+)-streptazolin 1 from aminocyclopentenol (-)-7 was 4.8% for a total of 16 steps.
Li
Fangzheng
F
Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556, USA.
Miller
Marvin J
MJ
D003500:Cyclization; D003517:Cyclopentanes / Q000737:chemistry; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D012825:Silicon / Q000737:chemistry*; D013237:Stereoisomerism
D003517:Cyclopentanes; D010880:Piperidines; C520587:aminocyclopentenol; C428165:streptazolin; D012825:Silicon