Relative stereochemical determination and synthesis of the C1-C17 fragment of a new natural polyketide.
The challenging determination of the relative stereochemistry of a complex natural polyketide portion was achieved. After careful NMR analysis, a concise synthesis of a set of possible relative diastereomers (only 6 diastereomers out of the 32 initially envisioned) has been carried out using a common strategy based on enantioselective aldol reactions. With a high predictability, final NMR comparison established the relative stereochemistry of the C1-C17 fragment of this natural product.
Fleury
Etienne
E
CNRS UMR 8638, Faculté de Pharmacie, Université Paris Descartes, 4 avenue de l'observatoire, 75270 Paris cedex 06, France.
Lannou
Marie-Isabelle
MI
Bistri
Olivia
O
Sautel
François
F
Massiot
Georges
G
Pancrazi
Ange
A
Ardisson
Janick
J
D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism
D001688:Biological Products; D018942:Macrolides