89102-36-3Relevant academic research and scientific papers
Synthesis of (-)-(5R,6S)-6-acetoxyhexadecanolide based on L-proline-catalyzed asymmetric aldol reactions
Ikishima, Hideaki,Sekiguchi, Yusuke,Ichikawa, Yoshiyasu,Kotsuki, Hiyoshizo
, p. 311 - 316 (2006)
A convenient method for proline-catalyzed asymmetric aldol reactions using synthons of straight-chain aliphatic aldehydes, and aldehydes bearing a 1,3-dithiane moiety at the β-position, has been developed. This method was successfully applied to the synthesis of (-)-(5R,6S)-6-acetoxyhexadecanolide, an oviposition attractant pheromone of the female Culex mosquito.
Stereoselective synthesis of (-)-(5R,6S)-6-acetoxy-5-hexadecanolide, the mosquito oviposition attractant pheromone
Wang, Zhi-Min,Qian, Xin-Hua,Zhou, Wei-Shan
, p. 1191 - 1198 (1990)
The natural mosquito oviposition attractant pheromone,(-)-(5R,6S)- 6-acetoxy-5-hexadecanolide (1) was synthesized from readily available 1,2-cyclohexanediol, using kinetic resolution of cyclic allylic alcohol by modified Sharpless asymmetric epoxidation reagent as the key step.
Synthesis of (-)-(5R,6S)-6-acetoxyhexadecan-5-olide by L-proline-catalyzed asymmetric aldol reactions
Sun, Bin,Peng, Lizeng,Chen, Xuesong,Li, Yulin,Li, Ying,Yamasaki, Kaori
, p. 1305 - 1307 (2005)
The natural mosquito attractant pheromone, (-)-(5R,6S)-6-acetoxyhexadecan- 5-olide 1, was synthesized from readily available aldehyde 3 and cyclopentanone 4 using L-proline catalyzed asymmetric aldol reactions as the key step.
AN ENANTIOSPECIFIC SYNTHESIS OF (-)-(5R,6S)-6-ACETOXY-5-HEXADECANOLIDE, THE MOSQUITO OVIPOSITION ATTRACTANT PHEROMONE
Kang, Suk-Fu,Cho, Il-Hwan
, p. 743 - 746 (1989)
(-)-(5R,6S)-6-Acetoxy-5-hexadecanolide, (-)-1, the natural mosquito oviposition attractant pheromone was synthesized from readily available carbohydrate, (-)-2-deoxy-D-ribose, using radical carbon-carbon bond formation as the key step.
Enantioselective synthesis of (-)-(5R,6S)-6-acetoxyhexadecan-5-olide via tandem α-aminooxylation-Henry reaction
Pandey, Rachana,Garg, Yuvraj,Prakash, Ranjana,Pandey, Satyendra Kumar
, p. 20 - 27 (2018/10/26)
novel enantioselective synthetic approach of (-)-(5R,6S)-6-acetoxyhexadecan-5-olide, an oviposition attractant pheromone of the mosquito Culex pipiens fatigans is presented, starting from n-dodecanal. The synthesis features tandem α-aminooxylation-Henry a
Enantioselective synthesis of mosquito oviposition pheromone and its epimer from a naturally occurring fatty acid
Hurem, David,Dudding, Travis
, p. 101732 - 101739 (2015/12/08)
The synthesis of Mosquito Oviposition Pheromones (MOP) (5R,6S)-5-acetoxy-6-hexadecanolide and its unnatural (5R,6R)-diastereomer in 68% and 54% overall yield by a route involving an organocatalyzed epoxidation of naturally occurring cis-5-hexadecenoic acid and diastereodivergent esterification is reported. The investigation of a dynamic kinetic asymmetric transformation (DYKAT) as an alternate strategy for preparing the target MOPs is also discussed, however this approach was unsuccessful due to the formation of a ketone by-product that inhibited the lipase mediated acetylation step of the DYKAT process.
Asymmetric total synthesis of all four isomers of 6-acetoxy-5- hexadecanolide: The major component of mosquito oviposition attractant pheromones
Dong, Hong-Bo,Yang, Ming-Yan,Zhang, Xiao-Teng,Wang, Ming-An
, p. 610 - 616 (2014/05/20)
An asymmetric total synthesis of (5S,6R)-(+)-erythro-6-acetoxy-5- hexadecanolide 1a has been accomplished from readily available hex-5-yn-1-ol via Shi's asymmetric epoxidation as the key step, in eight steps with an overall yield of 33.5%. In addition, the stereoselective synthesis of all four isomers of 6-acetoxy-5-hexadecanolide 1a-1d were obtained via Sharpless asymmetric dihydroxylation and Mitsunobu reaction as the key steps with overall yields of 16.5-21.2%, respectively.
Facile total synthesis of (-)-(5R,6S)-6-acetoxy-5-hexadecanolide from carbohydrate, a mosquito oviposition attractant pheromone
Das, Saibal,Mishra, Anand Kumar,Kumar, Ashish,Al Ghamdi, Ahamad Al Khazim,Yadav, Jhillu Singh
, p. 7 - 11 (2012/10/29)
Total synthesis of (-)-(5R,6S)-6-acetoxy-5-hexadecanolide, a major component of mosquito oviposition attractant pheromones is reported. The key synthetic steps involve epoxide opening by lithiated salt of ethylpropionate and acid catalysed lactonization.
Facile synthesis of (-)-6-acetoxy-5-hexadecanolide by size-selective ring-closing/cross metathesis
Quinn, Kevin J.,Curto, John M.,McGrath, Kevin P.,Biddick, Neal A.
scheme or table, p. 7121 - 7123 (2010/01/18)
A total synthesis of (-)-6-acetoxy-5-hexadecanolide, in six steps and 37% overall yield from (2R,3S)-1,2-epoxy-4-penten-3-ol is reported. The key synthetic step is a size-selective ring-closing/cross metathesis reaction in which lactone formation and alky
(R)-2,3-Cyclohexylideneglyceraldehyde, a novel template for stereoselective preparation of functionalized δ-lactones: Synthesis of mosquito oviposition pheromone
Dhotare, Bhaskar,Goswami, Dibakar,Chattopadhyay, Angshuman
, p. 6219 - 6221 (2007/10/03)
(R)-2,3-Cyclohexylideneglyceraldehyde 1 has been used to prepare functionalized δ-lactones. This was exemplified by a simple and efficient synthesis of the oviposition pheromone 10 of Culex pipens fatigans.
