477284-13-2

Upstream product

• 477284-12-1 C₂₆H₂₅ClO₃ 
• 108-24-7 acetic anhydride 
• 104-88-1 4-chlorobenzaldehyde 
• 14506-33-3 (S)-1-(4-chlorophenyl)-but-3-en-1-ol 

Downstream Products

• 477284-04-1 (2S,4R,6S)-2-[2-(4-Benzyloxy-phenyl)-ethyl]-4-bromo-6-(4-chloro-phenyl)-tetrahydro-pyran 
• 477284-05-2 (2R,6S)-2-[2-(4-Benzyloxy-phenyl)-ethyl]-6-(4-tert-butoxy-phenyl)-tetrahydro-pyran 
• 477284-09-6 (2S,6R)-6-[2-[4-(benzyloxy)phenyl]ethyl]-2-[4-(methoxy)phenyl]tetrahydropyran 
• 477284-06-3 (2S,6R)-6-[2-[4-(benzyloxy)phenyl]ethyl]-2-[4-(chloro)phenyl]tetrahydropyran 
• 30358-99-7 Centrolobin 

Relevant academic research and scientific papers

Synthesis of (-)-centrolobine by Prins cyclizations that avoid racemization.

[formula: see text] The segment-coupling Prins cyclization avoids two of the problems common to other Prins cyclization protocols: side-chain exchange and partial racemization by reversible 2-oxonia Cope rearrangement. Model studies demonstrate the stereochemical fidelity of Prins cyclizations using alpha-acetoxy ethers compared with direct aldehyde-alcohol Prins reactions. Furthermore, we propose a mechanism for the racemization observed in some intermolecular Prins cyclizations. Two straightforward syntheses of optically pure (-)-centrolobine highlight the utility of Prins cyclizations.