THE SYNTHESIS OF C3-METHYL, C3-DECARBOXY-ZARAGOZIC ACID-A - A POTENT SQUALENE SYNTHASE INHIBITOR

Authors
KUO CH PLEVYAK SP BIFTU T PARSONS WH BERGER GD
Citation
Ch. Kuo et al., THE SYNTHESIS OF C3-METHYL, C3-DECARBOXY-ZARAGOZIC ACID-A - A POTENT SQUALENE SYNTHASE INHIBITOR, Tetrahedron letters, 34(43), 1993, pp. 6863-6866
Citations number
10
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
43
Year of publication
1993
Pages
6863 - 6866
Database
ISI
SICI code
0040-4039(1993)34:43<6863:TSOCCA>2.0.ZU;2-S
Abstract
The tide compound and its C4-pivaloyloxy methyl (POM) ester have been synthesized by converting zaragozic acid A to the kev intermediate of the protected C3-hydroxymethyl compound 6. Subsequent radical deoxygen ation via the Barton-McCombie procedure, followed by deprotection, aff orded the product 11 (L-703,370). This compound possesses squalene bio synthesis inhibitory potency of 22% at 24 mpk and its C4-POM ester, 12 (L-735,142), exhibits an ED50 of 1.6 mpk in our oral mouse assay.