ChemInform Abstract: Synthesis of (R)- and (S)-3-(tert-Butyldimethylsilyloxy)-1-pyrroline N-Oxides — Chiral Nitrones for Synthesis of Biologically Active Pyrrolidine Derivative, Geissman—Waiss Lactone.

✍ Scribed by S.-I. MURAHASHI; H. OHTAKE; Y. IMADA

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 36 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199829133

✦ Synopsis

Synthesis of (R)-and (S)-3-(tert-Butyldimethylsilyloxy)-1-pyrroline N-Oxides -Chiral Nitrones for Synthesis of Biologically Active Pyrrolidine Derivative, Geissman-Waiss Lactone.

-Tungstatemediated oxidation of the chiral Tbs-protected 3-hydroxypyrrolidines (II) provides the required nitrones (III). They are especially useful for the preparation of pyrrolidine alkaloids. As an example, the conversion of (R)-(III) to the Geissman-Waiss lactone (X) is described. -(MURAHASHI, S.-I.; OHTAKE,