Chiron approach from D-mannitol to access a diastereomer of the reported structure of an acetogenin, an amide alkaloid and a sex pheromone.
Carbohydr Res
; 473: 5-11, 2019 Feb 01.
Article
en En
| MEDLINE
| ID: mdl-30590155
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.
Palabras clave
Texto completo:
1
Colección:
01-internacional
Banco de datos:
MEDLINE
Asunto principal:
Atractivos Sexuales
/
Alcaloides
/
Acetogeninas
/
Amidas
/
Manitol
Límite:
Animals
Idioma:
En
Revista:
Carbohydr Res
Año:
2019
Tipo del documento:
Article
País de afiliación:
India