| Title: | "Chiron approach from D-mannitol to access a diastereomer of the reported structure of an acetogenin, an amide alkaloid and a sex pheromone" |
| Author(s): | Chatterjee S; Manna A; Chakraborty I; Bhaumik T; |
| Address: | "Department of Chemistry, Jadavpur University, Jadavpur, Kolkata, 700032, West Bengal, India. Department of Chemistry, Jadavpur University, Jadavpur, Kolkata, 700032, West Bengal, India. Electronic address: tanurimabhaumik@gmail.com" |
| DOI: | 10.1016/j.carres.2018.12.008 |
| ISSN/ISBN: | 1873-426X (Electronic) 0008-6215 (Linking) |
| Abstract: | "A short, simple and convenient chiron approach to (3R,4S,5R)-(-)-3,5-dihydroxy-4-decanolide, a hitherto unknown diastereomer of the reported structure of a naturally occurring acetogenin, (+)-polyporolide has been accomplished starting from a commercially available, inexpensive chiral pool molecule D-(+)-mannitol in nine efficient steps. An advanced intermediate synthesized from D-(+)-mannitol in six steps toward this end was further employed successfully to access two different natural products bearing two contiguous stereogenic centers. As a result, first chiron approach to formal total synthesis of an amide alkaloid, (4R,5R,2E)-4,5-dihydroxy-1-(piperidin-1-yl)dec-2-en-1-one and total synthesis of a male sex pheromone in parasitic Hymenoptera, (4R,5R)-(-)-5-hydroxy-4-decanolide have also been achieved" |
| Keywords: | Acetogenins/*chemistry Alkaloids/*chemistry Amides/*chemistry Animals Hymenoptera Male Mannitol/*chemistry Sex Attractants/*chemistry Stereoisomerism Chiral pool molecule Chiral template Chiron approach D-(+)-mannitol Formal synthesis Total synthesis; |
| Notes: | "MedlineChatterjee, Sandip Manna, Avrajit Chakraborty, Ipsita Bhaumik, Tanurima eng Netherlands 2018/12/28 Carbohydr Res. 2019 Feb 1; 473:5-11. doi: 10.1016/j.carres.2018.12.008. Epub 2018 Dec 14" |
