Synthesis of Tribolure, the Common Aggregation Pheromone of Four Tribolium Flour Beetles

Publisher: John Wiley & Sons Inc

E-ISSN: 1614-7065|33|6|627-631

ISSN: 1001-604x

Source: CHINESE JOURNAL OF CHEMISTRY (ELECTRONIC), Vol.33, Iss.6, 2015-06, pp. : 627-631

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Abstract

AbstractHerein we report a synthesis of the natural tribolure, an aggregation pheromone which consists of (4R,8S)‐, (4R,8R)‐, (4S,8S)‐, and (4S,8R)‐4,8‐dimethyldecanals in a ratio of 4/4/1/1, from (R)‐4‐methyl‐δ‐valerolactone, a byproduct of the degradation of steroidal sapogenins. Merging the stereoisomers of the same ratios into one synthetic target and using the same chiron for the construction of the C4 stereocenters are notable features of this synthesis.