A model study toward the total synthesis of N-deacetyllappaconitine.
[reaction: see text] A model study leading to the preparation of the AEF rings of N-deacetyllappaconitine is described. The conjugate addition to the alpha-alkyl cyclohexenone 10 proceeded with high diastereocontrol. The Mannich cyclization of 16 to 4 was accomplished by heating with Rexyn-300 and Na(2)SO(4).
Taber
Douglass F
DF
Department of Chemistry and Biochemistry, University of Delaware, Newark, 19716, USA. taberdj@udel.edu
Liang
Jiang-Lin
JL
Chen
Bei
B
Cai
Lisi
L
D000157:Aconitine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000478:Alkylation; D003500:Cyclization; D003510:Cyclohexanes / Q000737:chemistry; D053138:Cyclohexenes; D006838:Hydrocarbons / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure
D003510:Cyclohexanes; D053138:Cyclohexenes; D006838:Hydrocarbons; C055260:N-deacetyllappaconitine; C052568:cyclohexene; C030011:carbene; D008697:Methane; D000157:Aconitine