Synthesis p. 1151 - 1160 (1997)
Update date:2022-08-11
Topics:
Weymann, Markus
Pfrengle, Waldemar
Schollmeyer, Dieter
Kunz, Horst
Aldimines of 2,3,4,6-tetra-O-pivaloyl-β-D-galactosylamine react with 1-methoxy-3-trimethylsilyloxybuta-1,3-diene in a Mannich-Michael condensation reaction sequence to give 2-substituted N-galactosyl-5,6-dehydropiperidin-4-ones 3 with high diastereoselectivity. The X-ray analysis of the 2-propyl derivative 3a proved (R)-configuration of the major diastereomer and led to the correction of our earlier assignment of configuration for (-)-coniine hydrochloride 9a obtained from this intermediate. Despite their low reactivity, these enaminones 3 can be converted into chiral 2,6-cis-disubstituted piperidinones 12 with high stereoselectivity by reaction with organocuprates in combination with hard electrophiles. Enantiomerically pure alkaloids such as (-)-dihydropinidine and gephyrotoxine 167B have been synthesized according to this methodology.
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