A concise total synthesis of (-)-cylindricine C through a stereoselective intramolecular aza-[3 + 3] annulation strategy.
[reaction: see text] An enantioselective total synthesis of (-)-cylindricine C is described, featuring a diastereoselective intramolecular aza-[3 + 3] annulation strategy and an interesting halohydrin formation of the C4-5 olefin for construction of C4-ketone. This work provides a unique approach to this family of natural products.
Division of Pharmaceutical Sciences and Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53705, USA.
Jacob J
JJ
Swidorski
Jiashi
J
Wang
Richard P
RP
Hsung
D001372:Aza Compounds / Q000737:chemistry*; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D015363:Quinolones / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D001372:Aza Compounds; D006575:Heterocyclic Compounds, 3-Ring; D015363:Quinolones; C485391:cylindricine C