✦ LIBER ✦
Chemo-enzymatic enantio-convergent asymmetric total synthesis of (S)-(+)-dictyoprolene using a kinetic resolution—stereoinversion protocol
✍ Scribed by Andreas Wallner; Harald Mang; Silvia M. Glueck; Andreas Steinreiber; Sandra F. Mayer; Kurt Faber
- Publisher
- Elsevier Science
- Year
- 2003
- Tongue
- English
- Weight
- 214 KB
- Volume
- 14
- Category
- Article
- ISSN
- 0957-4166
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✦ Synopsis
A single enantiomer of a (stereo)chemically labile allylic-homoallylic alcohol was obtained in 91% e.e. and 96% yield from the racemate by employing a lipase-catalysed kinetic resolution coupled to in situ inversion under carefully controlled (Mitsunobu) conditions in order to suppress side reactions, such as elimination and racemisation. This technique was successfully applied to an enantio-convergent asymmetric total synthesis of the algal fragrance component (S)-dictyoprolene.