Synthesis of cribrostatin 6

Journal of Organic Chemistry

Volumn 73, Issue 19, 2008, Pages 7441-7443

  Markey, Michael D ^a   Kelly, T Ross ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS;

CHEMICAL EQUATIONS; INTRAMOLECULAR CYCLIZATION; REGIOSELECTIVE BROMINATION;

SYNTHESIS (CHEMICAL);

CRIBROSTATIN; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; MOLECULAR INTERACTION; ORGANIC CHEMISTRY; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

ANTI-INFECTIVE AGENTS; ANTINEOPLASTIC AGENTS; BIOLOGICAL PRODUCTS; CYCLIZATION; HALOGENATION; ISOQUINOLINES;

EID: 53049085767     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801694w     Document Type: Article

References (16)

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11. For a three-step conversion of 9 to 10, see ref 4.
12. Finkelstein, B. L. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; John Wiley: Chichester, UK, 1995; Vol. 1, p 686.
13. The structure of 11 was confirmed by X-ray crystallography (see the Supporting Information).
14. Cursory attempts to achieve a palladium-catalyzed cross-coupling reaction between 11 and 7 failed to give any of the desired biaryl product i. Compounds 11 and 6 (protodestannylated 7) were recovered from the reaction mixture. (Chemical Equation Presented)
15. For a recent review, see: Espinet, P.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704-4734.
16. Phenol 10 is somewhat unstable to the reaction conditions. A better yield of 10 is obtained if the reaction is not run to completion.