Enantioselective total synthesis of aspidophytine.
[structure: see text] An enantioselective total synthesis of aspidophytine is described. The indole fragment bearing a cis-alkene substituent was efficiently prepared through radical cyclization of a 2-alkenylphenylisocyanide followed by Sonogashira coupling of the generated 2-iodoindole derivative with a functionalized acetylene unit. After formation of the 11-membered cyclic amine, the aspidosperma skeleton and lactone ring were constructed to complete the total synthesis.
Sumi
Shinjiro
S
Graduate School of Pharmaceutical Sciences, The University of Tokyo, and PRESTO, JST, 7-3-1 Hongo, Bunkyo-ku, Tokyo113-0033, Japan.
Matsumoto
Koji
K
Tokuyama
Hidetoshi
H
Fukuyama
Tohru
T
D000114:Acetylene; D003500:Cyclization; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D026121:Indole Alkaloids; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D018515:Plant Leaves / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry; D013237:Stereoisomerism
D006576:Heterocyclic Compounds, 4 or More Rings; D007202:Indicators and Reagents; D026121:Indole Alkaloids; D007211:Indoles; C476906:aspidophytine; D000114:Acetylene