179261-04-2Relevant academic research and scientific papers
Asymmetric total synthesis of the Caribbean fruit fly pheromone (+)-epianastrephin
Schultz, Arthur G.,Kirincich, Steven J.
, p. 5626 - 5630 (2007/10/03)
An asymmetric total synthesis of (+)-epianastrephin (1) from the chiral benzamide 2 (15 steps, 9.5% overall yield) is described. Birch reduction-alkylation of 2 with methyl iodide gave 3 in 91% yield as a single diastereomer. Cyclohexadiene 3 was converted to olefinic carboxylic acid 6b, and a tandem iodolactenization-radical reduction sequence provided lactone 8 with three contiguous stereogenic centers. Chiral HPLC comparison of diol 12b, the immediate precursor to (+)-epianastrephin (1), with 12b prepared from racemic epianastrephin demonstrated that 1 had been prepared with > 98% ee.
