| Title: | Thiopyran route to polypropionates: an efficient synthesis of serricornin |
| Author(s): | Ward DE; Jheengut V; Beye GE; |
| Address: | "Department of Chemistry, University of Saskatchewan, 110 Science Place, Saskatoon SK S7N 5C9, Canada. dale.ward@usask.ca" |
| ISSN/ISBN: | 0022-3263 (Print) 0022-3263 (Linking) |
| Abstract: | "The synthesis of serricornin [(4S,6S,7S)-7-hydroxy-4,6-dimethylnonan-3-one], a sex pheromone produced by the female cigarette beetle (Lasioderma serricorne F.), in seven steps from readily available racemic 1,4-dioxa-8-thiaspiro[4.5]decane-6-carboxaldehyde (6) is described. The key steps include enantioselective aldol reaction of 6 with tetrahydrothiopyran-4-one catalyzed by 5-[(2S)-pyrrolidine-2-yl]-1H-tetrazole to fabricate the tetrapropionate skeleton, stereoselective Li(s)Bu(3)BH reduction of the resulting aldol adduct, Barton-McCombie deoxygenation, and Raney nickel desulfurization" |
| Keywords: | Ketones/*chemical synthesis/chemistry Molecular Structure Propionates/*chemical synthesis/chemistry Pyrans/*chemistry Stereoisomerism Sulfhydryl Compounds/*chemistry; |
| Notes: | "MedlineWard, Dale E Jheengut, Vishal Beye, Garrison E eng Research Support, Non-U.S. Gov't 2006/11/04 J Org Chem. 2006 Nov 10; 71(23):8989-92. doi: 10.1021/jo061747w" |
