Asymmetric formal synthesis of schulzeines A and C.
The asymmetric formal synthesis of schulzeines A and C is described. Key features of the synthesis include the efficient and stereoselective construction of the benzoquinolizidine skeleton via the aza-Claisen rearrangement-induced ring expansion of the 1-vinyl-N-glycyl-isoquinoline, which was prepared by the highly enantioselective asymmetric allylation of the 8-benzyloxy-substituted dihydroisoquinoline and by the acid-catalyzed transannulation of the resulting 10-membered lactam.
College of Pharmacy, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 151-742, Korea.
Jaebong
J
Jang
Jong-Wha
JW
Jung
Jaeseung
J
Ahn
Jaehoon
J
Sim
Dong-Jo
DJ
Chang
Dae-Duk
DD
Kim
Young-Ger
YG
Suh
D003500:Cyclization; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis*; D007769:Lactams / Q000138:chemical synthesis*; D015394:Molecular Structure; D054837:Quinolizidines / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013463:Sulfuric Acid Esters / Q000138:chemical synthesis*
D006575:Heterocyclic Compounds, 3-Ring; D007769:Lactams; D054837:Quinolizidines; D013463:Sulfuric Acid Esters; C541694:schulzeine A; C523672:schulzeine C