Enantioselective total synthesis of pyrinodemin A.
Pyrinodemin A 1, a cytotoxic marine alkaloid, was synthesized in a convergent and enantioselective fashion. The key steps are an asymmetric intramolecular dipolar cycloaddition of an oxazoline N-oxide to introduce the bicyclic ring system of the molecule, a cuprate coupling for the extension of the saturated chain and a B-alkyl Suzuki coupling for the introduction of a 3-pyridyl moiety. Reductive amination allowed the coupling of the second side-chain onto the nitrogen atom to give 1. Additionally, attempts to prepare 1 from a trienic precursor by a double B-alkyl Suzuki reaction are described.
Pouilhès
Annie
A
Laboratoire de Chimie des Procédés et Substances Naturelles, Institut de Chimie Moléculaire et des Matériaux dOrsay UMR CNRS no 8182, Bâtiment 410, Univ. Paris-Sud 11, F-91405 Orsay, France.
Amado
Anel Florès
AF
Vidal
Anne
A
Langlois
Yves
Y
Kouklovsky
Cyrille
C
D008968:Molecular Conformation; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D010080:Oxazoles; D011725:Pyridines; C430117:pyrinodemin A