Bidirectional Synthesis of 6-Acetoxy-5-hexadecanolide, the Mosquito Oviposition Pheromone of Culex quinquefasciatus, from a C2-Symmetric Building Block Using Olefin Metathesis Reactions,The Journal of Organic Chemistry

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Bidirectional Synthesis of 6-Acetoxy-5-hexadecanolide, the Mosquito Oviposition Pheromone of Culex quinquefasciatus, from a C2-Symmetric Building Block Using Olefin Metathesis Reactions
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2018-01-12 00:00:00 , DOI: 10.1021/acs.joc.7b02944
Bernd Schmidt ₁ , Monib H. Petersen ₁ , Diana Braun ₁

Affiliation

(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 C₂-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.

中文翻译：

利用烯烃复分解反应从C ₂对称结构单元双向合成6-乙酰氧基-5-十六烷化物（Culex quinquefasciatus的蚊子产卵信息素）

（5 R，6 S）-6-乙酰氧基-5-十六烷化物（MOP）是蚊子Cx的产卵信息素。quinquefasciatus，一种引起多种热带疾病的病原体。我们在此描述和评估了从甘露醇衍生的（3 R，4 R）-六-1,5-二烯-3,4-二醇开始的MOP的三种合成。该C ₂对称结构单元是通过双向烯烃复分解反应制成6-表位的-MOP，通过Mitsunobu反演将其转换为MOP。这三种途径中最短的途径是利用两个顺序的交叉复分解反应和辅助的串联催化烯烃还原反应，这是由Ru-卡宾就地转化为Ru-氢化物引起的。

更新日期：2018-01-12

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