cis-decalins from quinic acid: toward a synthesis of branimycin.
[reaction: see text] Starting from (-)-quinic acid an efficient synthesis of highly functionalized cis-alpha,beta-unsaturated ketone 3, an advanced precursor of branimycin, has been accomplished via two key step reactions: a ring closing metathesis reaction to prepare the cis-decalin system, and a highly stereoselective epoxidation reaction.
Marchart
Stefan
S
Institut für Organische Chemie, Währingerstrasse 38, A-1090 Wien, Austria.
Mulzer
Johann
J
Enev
Valentin S
VS
D004852:Epoxy Compounds / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D011801:Quinic Acid / Q000737:chemistry*
D004852:Epoxy Compounds; D007659:Ketones; D018942:Macrolides; D009281:Naphthalenes; C516575:branimycin; D011801:Quinic Acid; C007229:decalin