107736-23-2Relevant academic research and scientific papers
Total synthesis and antifungal activity of (2S,3R)-2-aminododecan-3-ol
Vijai Kumar Reddy,Prabhavathi Devi,Prasad,Poornima,Ganesh Kumar
, p. 4678 - 4680 (2012)
We report the total synthesis of (2S,3R)-2-aminododecan-3-ol has been achieved starting from commercially available 10-undecenoic acid. The key steps involved are Sharpless asymmetric epoxidation, Miyashita's boron-directed C-2 regioselective azidolysis, generated the asymmetric centers and in situ detosylation and reduction of azido tosylate. The antifungal activity of the synthesized (2S,3R)-2-aminododecan-3-ol was evaluated on several Candida strains and was comparable to miconazole, a standard drug.
Posticlure: A novel trans-epoxide as a sex pheromone component of the tussock moth, Orgyia postica (Walker)
Wakamura, Sadao,Arakaki, Norio,Yamamoto, Masanobu,Hiradate, Syuntaro,Yasui, Hiroe,Yasuda, Tetsuya,Ando, Tetsu
, p. 687 - 689 (2001)
A single EAG-active component was found in a pheromone extract from virgin females of the tussock moth, Orgyia postica. This compound named posticlure possesses a trans-epoxy ring and was identified as (6Z,9Z,11S,12S)-11,12-epoxyhenicosa-6,9-diene by means of GC-MS, 1H NMR and chiral HPLC analyses, and further chemical derivation followed by the GC-MS analysis. In a field test with the pheromone synthesized stereoselectivity, the male moths were specifically attracted to the (11S,12S)-isomer but not to the antipode.
Synthesis of the optical antipodes of 4-alkyl-γ-lactones
Thijs, Lambertus,Waanders, Peter P.,Stokkingreef, Edwin H. M.,Zwanenburg, Binne
, p. 332 - 337 (2007/10/02)
Optical antipodes of 4-alkyl-γ-lactones 3 have been prepared by photochemical rearrangement of optically active α,β-epoxy diazomethyl ketones 1 in ethanol to give 4-hydroxy-alkenoates 2, followed by reduction of the alkene bond and subsequent lactonization.The required epoxy diazomethyl ketones 1 were obtained via the following sequence of reactions: alkylation of 2-propyn-1-ol, subsequent reduction to the alkenols 6, Sharpless epoxidation to 2,3-epoxy alcohols 7, oxidation to glycidic esters 8 and finally conversion to diazo ketones 1.The enantiomeric purities range from 84 to 100percent.
