skip to main content
Language:
Search Limited to: Search Limited to: Resource type Show Results with: Show Results with: Index

Farnesyl chain modification of squalene synthase inhibitor benzylfarnesylamine: Conversion to the terminal bis(trifluoromethyl) derivative

Jewell, Charles F ; Brinkman, John ; Petter, Russell C ; Wareing, James R

Tetrahedron, 1994, Vol.50(13), pp.3849-3856 [Peer Reviewed Journal]

Full text available

View all versions
Citations Cited by
  • Title:
    Farnesyl chain modification of squalene synthase inhibitor benzylfarnesylamine: Conversion to the terminal bis(trifluoromethyl) derivative
  • Author: Jewell, Charles F ; Brinkman, John ; Petter, Russell C ; Wareing, James R
  • Description: Potent squalene synthase inhibitor 1 was converted to the bis(trifluoromethyl) analog 14 in 11% overall yield for 9 steps. The amine nitrogen of 1 was protected with the 2-(trimethylsilyl)ethoxycarbonyl (TEOC) protecting group. The 10,11 olefin was selectively epoxidized, cleaved and converted to the phosphonium salt 6 . The ylid from 6 underwent a Wittig condensation with hexafluoroacetone to give the TEOC containing olefin 8 . Tetrabutylammonium fluoride or HF could not remove the TEOC group without isomerizing the 10,11 olefin of the farnesyl chain to the E-9,10 olefin. The bis(trifluoromethyl) olefin of 8 is very sensitive to either acidic or basic conditions. However, it was found that BF 3 ·Et 2 O could remove the TEOC group without the undesired isomerization to give 14 . Graphic
  • Is Part Of: Tetrahedron, 1994, Vol.50(13), pp.3849-3856
  • Identifier: ISSN: 0040-4020 ; E-ISSN: 1464-5416 ; DOI: 10.1016/S0040-4020(01)89661-7
  • Subjects: Chemistry
  • Language: English

Searching Remote Databases, Please Wait