645390-02-9

Upstream product

• 89980-69-8 3,4-dimethoxyphenylmagnesium bromide 
• 645389-88-4 (2R,10S)-(+)-2-triisopropylsiloxy-octahydro-quinolizin-4-one 
• 645389-99-7 (2S,4R)-(+)-4-triisopropylsiloxy-2-(4'-N,O-di(benzyloxycarbonyl)hydroxylaminobutyl)cyclopentan-1-one 
• 645390-01-8 (5aS,7R)-(-)-7-triisopropylsiloxy-2,3,4,5,5a,6,7,8-octahydrocyclopent[b]azepine-N-oxide 
• 645389-89-5 (4S)-(-)-4-triisopropylsilyloxy-2-cyclopenten-1-one 
• 645390-09-6 (1R,4S)-(-)-4-triisopropylsilyloxy-1-hydroxycyclopent-2-ene 
• 13154-24-0 triisopropylsilyl chloride 
• 645390-11-0 (3R)-5-(4'-benzyloxy-1'-hydroxybutyl)-3-triisopropylsiloxycyclopentanone 
• 645389-93-1 (3R)-(+)-5-(4'-benzyloxybutylidene)-3-triisopropylsiloxycyclopentanone 
• 645389-91-9 (4R)-(+)-1-triethylsiloxy-4-triisopropylsilyloxy-cyclopentene 
• 645389-97-5 (3R,5S)-(+)-5-(4'-azidobutyl)-3-triisopropylsiloxycyclopentanone 
• 645389-95-3 (3R,5S)-(+)-5-(4'-hydroxybutyl)-3-triisopropylsiloxycyclopentanone 
• 115074-48-1 (1R,4S)-(-)-4-triisopropylsilyloxy-2-cyclopenten-1-ol acetate 

Downstream Products

• 386285-44-5 (2R,4S,9aS)-2-hydroxy-4-(3,4-dimethoxyphenyl)-decahydroquinolizidine 

Relevant academic research and scientific papers

Ring Expansive Routes to Quinolizidine Alkaloids: Formal Synthesis of (-)-Lasubine II

(Equation presented) The application of two nitrogen ring expansion reactions to lasubine alkaloid synthesis is reported. The approach involves a conjugate reduction/ alkylation sequence carried out on triisopropylsilyl- protected (S)-4-(-)-hydroxycyclopentenone, the formation of the quinolizidone ring system through nitrogen ring expansion, and the addition of an arylmetallic species to the resulting lactam. This work resulted in the preparation of 2-epA-lasubine II and a formal synthesis of lasubine II.