Article ID Journal Published Year Pages File Type
1348251 Tetrahedron: Asymmetry 2007 4 Pages PDF
Abstract

Enantiospecific synthesis of 12-methoxyneorogiola-1,3,5,7(17),8-pentaene, containing the complete carbon framework of the natural diquinane diterpenes neorogioldiols, starting from (S)-campholenaldehyde is described.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide

(1R,4R,5R)-4,7,8,8-Tetramethylbicyclo[3.3.0]oct-6-en-3-oneC12H18O[α]D22=-41.5 (c 5.9, CHCl3)Source of chirality: campholenaldehydeAbsolute configuration: (1R,4R,5R)

(1R,3S,4R,5R)-3-Methoxy-4,7,8,8-tetramethylbicyclo[3.3.0]oct-6-eneC13H22O[α]D23=-23.9 (c 16.2, CHCl3)Source of chirality: campholenaldehydeAbsolute configuration: (1R,3S,4R,5R)

(1R,5R,6R,7S)-7-Methoxy-2,2,6-trimethylbicyclo[3.3.0]oct-3-en-3-yl 4-methylphenyl ketoneC20H26O2[α]D25=-32.4 (c 5.1, CHCl3)Source of chirality: campholenaldehydeAbsolute configuration: (1R,5R,6R,7S)

(1R,5R,6R,7S)-7-Methoxy-2,2,6-trimethyl-3-[1-(4-methylphenyl)ethenyl]-bicyclo[3.3.0]oct-3-eneC21H28O[α]D24=-26.5 (c 2.0, CHCl3)Source of chirality: campholenaldehydeAbsolute configuration: (1R,5R,6R,7S)

Related Topics
Physical Sciences and Engineering Chemistry Inorganic Chemistry
Authors
, ,