| Title: | A direct stereoselective preparation of a fish pheromone and application of the zinc porphyrin tweezer chiroptical protocol in its stereochemical assignment |
| Author(s): | Ouedraogo YP; Huang L; Torrente MP; Proni G; Chadwick E; Wehmschulte RJ; Nesnas N; |
| Address: | "Department of Chemistry, Florida Institute of Technology, Melbourne, Florida 32901, USA" |
| ISSN/ISBN: | 1520-636X (Electronic) 0899-0042 (Linking) |
| Abstract: | "A two-step stereoselective preparation of a goldfish pheromone, 17alpha,20beta-dihydroxy-4-pregnen-3-one, is reported from the readily available cortexolone in 64% overall yield. The (20S)-epimer was also synthesized in three steps from cortexolone with an overall yield of 47%. A microscale chiroptical technique based on a host/guest complexation mechanism between the substrate and a dimeric metalloporphyrin host (tweezer) was used to confirm the stereochemical assignment, while Density Functional Theory (DFT) calculations were employed to explain the high stereoselectivity induced by the 17alpha-hydroxyl and C18-methyl groups" |
| Keywords: | Animals Circular Dichroism Goldfish Hydroxyprogesterones/*chemical synthesis/chemistry Metalloporphyrins/*chemistry Molecular Structure *Optical Tweezers Optics and Photonics/instrumentation/methods Pheromones/chemical synthesis/*chemistry *Quantum Theory; |
| Notes: | "MedlineOuedraogo, Yannick P Huang, Longchuan Torrente, Mariana P Proni, Gloria Chadwick, Ekaterina Wehmschulte, Rudolf J Nesnas, Nasri eng Research Support, Non-U.S. Gov't 2013/06/27 Chirality. 2013 Sep; 25(9):575-81. doi: 10.1002/chir.22186. Epub 2013 Jun 26" |
