Total synthesis and structural revision of the marine macrolide neopeltolide.
J Am Chem Soc
; 130(3): 804-5, 2008 Jan 23.
Article
en En
| MEDLINE
| ID: mdl-18161979
ABSTRACT
The total synthesis and structural revision of the marine natural product neopeltolide is reported. The key bond-forming step involves a Lewis acid-catalyzed intramolecular cyclization to install the tetrahydropyran ring and the macrocycle simultaneously. This type of cyclization is the first of its kind and assembles the carbon backbone of the natural product efficiently. The synthesis of the reported structure revealed differences in the data between the natural and synthetic material. After significant investigation, the diastereomeric molecule with the C11 and C13 configurations inverted was synthesized using the initial route. This compound matches the data reported for neopeltolide (1H, 13C, HRMS, IR, NOESY, [alpha]), thereby establishing the correct overall structure for this potent macrolide natural product, including the relative and absolute stereochemistry.
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Colección:
01-internacional
Banco de datos:
MEDLINE
Asunto principal:
Poríferos
/
Macrólidos
/
Antineoplásicos
Límite:
Animals
Idioma:
En
Revista:
J Am Chem Soc
Año:
2008
Tipo del documento:
Article
País de afiliación:
Estados Unidos