TY  - JOUR
A1  - Schmidt, Bernd
A1  - Petersen, Monib H.
A1  - Braun, Diana
T1  - Bidirectional Synthesis of 6-Acetoxy-5-hexadecanolide, the Mosquito Oviposition Pheromone of Culex quinquefasciatus, from a C-2-Symmetric Building Block Using Olefin Metathesis Reactions
JF  - The journal of organic chemistry
N2  - (5R,6S)-6-Acetoxy-5-hexadecanolide (MOP) is the oviposition pheromone of the mosquito Cx. quinquefasciatus, a vector of pathogens causing a variety of tropical diseases. We describe and evaluate herein three syntheses of MOP starting from mannitol-derived (3R,4R)-hexa-1,5-diene-3,4-diol. This C-2-symmetric building block is elaborated through bidirectional olefin metathesis reactions into 6-epi-MOP, which was converted into MOP via Mitsunobu inversion. The shortest of the three routes makes use of two sequential cross-metathesis reactions and an assisted tandem catalytic olefin reduction, induced by an in situ conversion of a Ru-carbene to a Ru-hydride.
Y1  - 2018
U6  - https://doi.org/10.1021/acs.joc.7b02944
SN  - 0022-3263
VL  - 83
IS  - 3
SP  - 1627
EP  - 1633
PB  - American Chemical Society
CY  - Washington
ER  -