✍ Scribed by Beat Ernst; Beatrice Wagner
No coin nor oath required. For personal study only.
For the assignment of the configuration at C(8) and C(15) of the natural oviposition-deterring pheromone 1 in Rhagoletis cerasi L., the four possible stereoisomers of 1 are synthesized. By condensing the C, building blocks (5R)-4 and (5S)-4 with the boron enolates of the C,, building blocks (4S)-13 and (4R)-13, followed by decarboxylative dehydration, all stereoisomers of 16 are available (Scheme 5). Glucosylation of 16 followed by formation of the taurin amide gives, after deprotection, the four stereoisomers (8R,15R)-1, (8S,15R)-1, (8R,15S)-1, and (8S,15S)-l (Scheme 6).
') The enolate was prepared by addition of 9-borabicyclo[3.3.1]nonane (9-BBN) triflate to the thioester (4S)-13 in anhydrous CH2C12 containing (i-Pr),EtN at -78". After 1 h stirring at -78" and 1 h at 0", the enolate was cooled to -78" for the reaction with the aldehyde (5R)-4.
Arbitrary numbering.
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## Abstract A new synthesis of the ammonium salt 1c of (8__RS__,15__R__)‐__N__‐[(β‐D‐glucopyranosyloxy)‐8‐hydroxypalmitoyl]taurine, the oviposition‐deterring pheromone of the European cherry fruit fly __Rhagoletis cerasi__ L., was achieved by starting from 2,3,4,6‐tetra‐__O__‐pivaloyl‐α‐D‐glucopyra