| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1346451 | Tetrahedron: Asymmetry | 2011 | 4 Pages |
Enantiomerically pure (+)-(5S)-dihydroyashabushiketol 1a was obtained by the 1,3-dipolar cycloaddition of a nitrile oxide, generated from oxime 3b, to N-acryloyl bornane[10,2]sultam (2R)-2 (67%, 85% de, then crystallization 81%, 99% de), followed by reduction with DIBAL-H to aldehyde (−)-6a (67%), Wittig reaction to isoxazoline (E/Z)-7 (60%), and finally hydrolytic hydrogenation (62%).
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide
(5S)-DihydroyashabushiketolC19H22O2[α]D20=+13.6 (c 1.0, CHCl3)Absolute configuration: (5S)
1-{[(5R)-4,5-Dihydro-3-phenethylisoxazole-5-yl]carbonyl]hexahydro-8,8-dimethyl-3H-3a,6-methano-2,1-benzisothiazoleC22H28N2O4S[α]D20=-192.8 (c 1.0, CHCl3)Absolute configuration: (5R)
(5R)-Hydroxymethyl-3-phenethylisoxazolineC12H15NO2[α]D20=+102.0 (c 1.0, CHCl3)Absolute configuration: (5R)
(5R)-Bromomethyl-3-phenethylisoxazolineC12H14BrNO[α]D20=-38.5 (c 1.0, CHCl3)Absolute configuration: (5R)
(5R)-Formyl-3-phenethylisoxazolineC12H13NO2[α]D20=-119.8 (c 1.0, CHCl3)Absolute configuration: (5R)
