Studies toward the total synthesis of the cytotoxic sponge alkaloid pyrinodemin A.
[structure: see text]. The syntheses of the proposed structure of pyrinodemin A (1) and its cis double bond positional isomer (C15'-C16') in racemic form are described. The key reaction involved an intramolecular nitrone/double bond cycloaddition. Our results suggest that neither 1 nor its double positional isomer is the correct structure of pyrinodemin A
Baldwin
J E
JE
The Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford, OX1 3QY, UK. jack.baldwin@chem.ox.ac.uk
Romeril
S P
SP
Lee
V
V
Claridge
T D
TD
D000470:Alkaloids / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D010080:Oxazoles / Q000138:chemical synthesis*; D011725:Pyridines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000470:Alkaloids; D010080:Oxazoles; D011725:Pyridines; C430117:pyrinodemin A