Synthesis of all 16 stereoisomers of pinesaw fly sex pheromones--tools and tactics for solving problems in fluorous mixture synthesis.
[Reaction: see text]. The application of fluorous mixture synthesis (FMS) for accessing natural products and their stereoisomers was validated by the total synthesis of all 16 stereoisomers of the pine sawfly sex pheromone. Four fluorous p-methoxybenzyl groups were used as tags, and a "4-mix-4-split" approach was employed in a divergent synthesis. This paper presents the details of the FMS of pine sawfly sex pheromones with an emphasis on identification and solving of problems encountered when working with fluorous mixtures.
Dandapani
Sivaraman
S
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.
Jeske
Mario
M
Curran
Dennis P
DP
D000818:Animals; D002625:Chemistry, Organic / Q000379:methods; D005260:Female; D005461:Fluorine / Q000737:chemistry; D006927:Hymenoptera / Q000737:chemistry*; D012724:Sex Attractants / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D012724:Sex Attractants; D005461:Fluorine