Azabicycloalkenes as synthetic intermediates--synthesis of azabicyclo[X.3.0]alkane scaffolds.
A general method to synthesize functionalized azabicyclo[X.3.0]alkane scaffolds 5 is reported. Key intermediates are azabicycloalkenes such as 1 and 2, which are acylated with unsaturated carboxylic acids and subsequently submitted to tandem olefin metathesis. The resulting bicyclic heterocycles are versatile intermediates for different dipeptide mimetics and can be used as intermediates for natural products with indolizidine scaffolds or analogues thereof. [reaction: see text].
Büchert
Marina
M
Justus-Liebig Universität Giessen, Institut für Organische Chemie, Heinrich-Buff-Ring 58, 35392 Giessen, Germany.
Meinke
Sebastian
S
Prenzel
Alexander H G P
AH
Deppermann
Nina
N
Maison
Wolfgang
W
D000215:Acylation; D000473:Alkanes / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D001372:Aza Compounds / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry; D003500:Cyclization; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy
D000473:Alkanes; D000475:Alkenes; D001372:Aza Compounds; D002264:Carboxylic Acids; D007202:Indicators and Reagents