ChemInform Abstract: Auxiliary-Controlled Stereoselective Enolate Protonation: Enantioselective Synthesis of cis and trans Annulated Decahydroquinoline Alkaloids.

6533b853fe1ef96bd12aca3c

RESEARCH PRODUCT

ChemInform Abstract: Auxiliary-Controlled Stereoselective Enolate Protonation: Enantioselective Synthesis of cis and trans Annulated Decahydroquinoline Alkaloids.

Horst Kunz Markus Weymann Martin Schultz-kukula

subject

Pumiliotoxin C chemistry.chemical_compound Bicyclic molecule Chemistry Stereochemistry Enantioselective synthesis Stereoselectivity Protonation General Medicine Enone Cis–trans isomerism Conjugate

description

Abstract The diastereoselective synthesis of the octahydroquinoline enone precursor of pumiliotoxin C is achieved via tandem Mannich-Michael reaction on N-galactosyl imines. Conjugate cuprate addition to the bicyclic enone stereoselectively forms the trans annulated 4a- epi -pumiliotoxin C skeleton in the presence of the carbohydrate auxiliary, and the cis annulated pumiliotoxin C skeleton in its absence.

year	journal	country	edition	language
2010-06-18	ChemInform

https://doi.org/10.1002/chin.199901215

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