Studies for the total synthesis of amphidinolide P.
J Org Chem
; 78(10): 4762-78, 2013 May 17.
Article
en En
| MEDLINE
| ID: mdl-23590535
ABSTRACT
A convergent, enantiocontrolled total synthesis of the 15-membered macrolide, amphidinolide P, is described. The synthesis utilizes three nonracemic components for an efficient assembly of the macrolactone in 12 steps via the longest linear pathway. Key developments include studies of the Hosomi-Sakurai reaction for the formation of the C6-C7 bond, a "ligandless" palladium-mediated Stille cross-coupling of the vinylic stannane 4 and the alkenyl bromide 5 to produce a highly functionalized dienol, and a thermally induced, intramolecular lactonization via the late-stage formation of an intermediate α-acylketene.
Texto completo:
1
Colección:
01-internacional
Banco de datos:
MEDLINE
Asunto principal:
Macrólidos
Idioma:
En
Revista:
J Org Chem
Año:
2013
Tipo del documento:
Article
País de afiliación:
Estados Unidos