Tetrahedron Letters p. 7835 - 7838 (1998)
Update date:2022-08-05
Topics:
Weymann, Markus
Schultz-Kukula, Martin
Kunz, Horst
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.
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