HIGHLY Z-SELECTIVE SYNTHESIS OF FUNCTIONALIZED MONOTERPENOIDS VIA N-YLIDE [2,3]SIGMATROPIC REARRANGEMENT AND ITS APPLICATION TO 13-CIS-RETINOL

Authors
HONDA K YOSHII I INOUE S
Citation
K. Honda et al., HIGHLY Z-SELECTIVE SYNTHESIS OF FUNCTIONALIZED MONOTERPENOIDS VIA N-YLIDE [2,3]SIGMATROPIC REARRANGEMENT AND ITS APPLICATION TO 13-CIS-RETINOL, Chemistry Letters, (8), 1996, pp. 671-672
Citations number
31
Categorie Soggetti
Chemistry
Journal title
Chemistry Letters → ACNP
ISSN journal
03667022
Issue
8
Year of publication
1996
Pages
671 - 672
Database
ISI
SICI code
0366-7022(1996):8<671:HZSOFM>2.0.ZU;2-G
Abstract
Highly stereoselective elongation of a functionalized E isoprene unit on the Z terminal methyl of prenol was achieved by the N-ylide rearran gement of N-tiglyl-beta-methallyldimethylammonium salt. (E,Z)-Rearrang ement product was converted into 13-cis-retinol via useful conjugated triene isoprenoid synthon.