Synthesis of 7-Substituted Farnesyl Diphosphate Analogues

Organic Letters

Volumn 4, Issue 18, 2002, Pages 3027-3030

  Rawat, Diwan S ^a   Gibbs, Richard A ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENZYME INHIBITOR; FARNESYL DIPHOSPHATE; ISOPRENOID PHOSPHATE; P21(RAS) FARNESYL PROTEIN TRANSFERASE; P21(RAS) FARNESYL-PROTEIN TRANSFERASE; TRANSFERASE;

ANIMAL; ARTICLE; CHEMISTRY; DRUG ANTAGONISM; HUMAN; IC 50; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ALKYL AND ARYL TRANSFERASES; ANIMALS; ENZYME INHIBITORS; HUMANS; INHIBITORY CONCENTRATION 50; POLYISOPRENYL PHOSPHATES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0037026543     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026176i     Document Type: Article

References (17)

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12. For a recent study in this area, see: Zhou, C. Shao, Y.; Gibbs, R. A. Bioorg. Med. Chem. Lett. 2002, 12, 1417.
13. FPP analogue 4 has been prepared previously by another route: Sen, S. E.; Ewing, G. J. J. Org. Chem. 1997, 62, 3529.
14. 9b only a slight excess of the dianion was necessary to alkylate simple primary halides. However, Weiler and Huckin generated the sodium salt of methyl (rather than ethyl) acetoacetate in situ using sodium hydride and used this to generate the dianion. In contrast, we employ the commercially available sodium salt of ethyl acetoacetate (11) in our coupling reactions.
15. (b) Huckin, S. N.; Weiler, L. J. Am. Chem. Soc. 1974, 96, 1082.
16. Soichi, S.; Maruoka, K.; Yamamoto, H. Tetrahedron Lett. 1986, 42, 2203.
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