Stereoselective Conjugate Addition Directed by an Enantiomerically Pure Ketal. Preparation of the Cyclohexanone Fragment of N-Methylwelwitindolinone C Isothiocyanate
- 1 October 1998
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1998 (10) , 1105-1107
- https://doi.org/10.1055/s-1998-1886
Abstract
A cyclohexanone intermediate to be employed in the synthesis of the marine natural product N-methylwelwitindolinone C isothiocyanate has been prepared. The synthesis is diastereoselective for the production of the C12 quaternary center, which is obtained via a conjugate addition reaction directed by an adjacent chiral, nonracemic ketal. A single crystal X-ray analysis of a derivative of the final product established the absolute stereochemistry at C12.Keywords
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