Total synthesis of formamicin.
J Am Chem Soc
; 126(30): 9307-17, 2004 Aug 04.
Article
en En
| MEDLINE
| ID: mdl-15281821
ABSTRACT
The enantioselective total synthesis of the cytotoxic plecomacrolide natural product formamicin (1) is described. Key aspects of this synthesis include the efficient transacetalation reactions of MOM ethers 28 and 38 to form the seven-membered formyl acetals 29 and 39, a late-stage Suzuki cross-coupling reaction of the highly functionalized vinyl boronic acid 6 and vinyl iodide 7, a highly beta-selective glycosidation reaction of beta-hydroxy ketone 4 with 2,6-dideoxy-2-iodoglucopyranosyl fluoride 3, and the global desilylation of penultimate intermediate 77 mediated by in situ generated Et(3)N.2HF.
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Banco de datos:
MEDLINE
Asunto principal:
Macrólidos
Idioma:
En
Revista:
J Am Chem Soc
Año:
2004
Tipo del documento:
Article
País de afiliación:
Estados Unidos