Total synthesis of clavepictines A and B and pictamine.
[Structure: see text] A short route for assembling clavepictines A and B and pictamine is described, which features elaboration of its trisubstituted piperidine moiety via condensation of a beta-keto sulfone with an l-alanine-derived bromide and subsequent alkylative cyclization and construction of its quinolizidine skeleton via a diastereoselective intramolecular conjugate addition. The possible stereochemical course for this conjugate addition is discussed.
Yu
Shanghai
S
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
Pu
Xiaotao
X
Cheng
Tiejun
T
Wang
Renxiao
R
Ma
Dawei
D
D000470:Alkaloids / Q000138:chemical synthesis*; D000818:Animals; D018360:Crystallography, X-Ray; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis*; D008968:Molecular Conformation; D015394:Molecular Structure; D011807:Quinolizines / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014561:Urochordata / Q000737:chemistry
D000470:Alkaloids; D006574:Heterocyclic Compounds, 2-Ring; D011807:Quinolizines; C519346:clavepictine A; C519347:clavepictine B; C503072:pictamine