Stereoisomer libraries: total synthesis of all 16 stereoisomers of the pine sawfly sex pheromone by a fluorous mixture-synthesis approach.
All 16 stereoisomers of the sex pheromone of pine sawfly (3,7,11-trimethylundecanol propanoate ester) have been synthesized on a 10- to 20-mg scale by a split-parallel fluorous mixture-synthesis approach. Spectral data obtained for all 32 compounds (16 alcohols and the corresponding propionates) matched well with published data, thereby validating the fluorous-tag encoding of diastereoisomers. This fluorous-tag encoding method is recommended for the efficient synthesis of multiple stereoisomers for spectroscopic studies, biological tests, or other structure-function relationships.
Dandapani
Sivaraman
S
Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA.
Jeske
Mario
M
Curran
Dennis P
DP
D000818:Animals; D002625:Chemistry, Organic / Q000379:methods; D005260:Female; D005461:Fluorine / Q000737:chemistry; D006927:Hymenoptera; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012724:Sex Attractants / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D012724:Sex Attractants; D005461:Fluorine