Synthesis of the diazonamide A macrocyclic core via a Dieckmann-type cyclization.
[reaction: see text] Suzuki coupling of 18 and 30 affords 9 as an interconverting mixture of two atropisomers. Treatment with LDA at -23 degrees C affords the macrocyclic ketone 8 in 57% yield.
Vedejs
E
E
Department of Chemistry, University of Michigan, Ann Arbor, MI 48109, USA. edved@umich.edu
Zajac
M A
MA
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008387:Marine Toxins / Q000138:chemical synthesis* / Q000737:chemistry; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry
D000970:Antineoplastic Agents; D006576:Heterocyclic Compounds, 4 or More Rings; D007202:Indicators and Reagents; D008387:Marine Toxins; D010080:Oxazoles; C408862:diazonamide A