A short synthesis of (−)-(4R,5S)-sitophilure using the regio- and stereoselective reduction of 3-acyltetrahydrothiopyran-4-ones with baker's yeast

Baker's‐Yeast‐Mediated Reduction of Sulfur‐Containing Compounds

“…Fujisawa observed the baker's‐yeast‐mediated reduction of 3‐propionyltetrahydrothiopyran‐4‐one ( 53 ) to give exclusively (3 R ,4 S )‐4‐hydroxy‐3‐propionyltetrahydrothiopyran ( 54 ) in 66 % yield with excellent enantioselectivity (97 % ee ) 80. This highly regio‐ and stereoselective baker's yeast reduction was applied to the stereocontrolled synthesis of (4 R ,5 S )‐sitophilure ( 55 ), the aggregation pheromone of both the rice and maize weevils (Scheme ) 80…”

Syntheses of Aggregation Pheromones of the Palm Weevils Rhyncophorus vulneratus and R. phoenicis and of (+)-trans-Whiskey Lactone

“…The 1 H and 13 C NMR spectra and the optical rotation of this compound were in complete agreement with those of the natural product. 5a Treatment of the cyclic acetal 9 with propane-1,3-dithiol and boron trifluoride etherate 19 at 0°C gave the cyclic thioacetal 13, which on treatment with activated Raney nickel 20 in refluxing methanol gave alcohol 14 in 80% yield. Mitsunobu inversion of the free hydroxyl group by using diethyl azodicarboxylate, triphenylphosphine, and 4-nitrobenzoic acid gave the target molecule (3S,4S)-3methyloctan-4-ol (2).…”

O emprego de fermento de pão, Saccharomyces cerevisiae, na síntese de feromônios

“…A rota sintética que fornece os compostos 28 e 29 se baseia no emprego do fermento de pão para a obtenção de dois intermediários através da síntese convergente 23 (Esquema 7). O sulcatol, (S)-(+)-6-metil-hept-5-en-2-ol (1) foi obtido por Belan et al 3 pela redução microbiológica altamente estereosseletiva com S. cerevisae 3 de 6-metil-hept-5-en-2-ona (30). O isômero R, entretanto, foi obtido utilizando outro microrganismo.…”