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Chiron approach from D-mannitol to access a diastereomer of the reported structure of an acetogenin, an amide alkaloid and a sex pheromone

Author:
Chatterjee, Sandip, Manna, Avrajit, Chakraborty, Ipsita, Bhaumik, Tanurima
Source:
Carbohydrate research 2019 v.473 pp. 5-11
ISSN:
0008-6215
Subject:
Hymenoptera, alkaloids, diastereomers, males, mannitol, sex pheromones
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.
Agid:
6264000