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Synlett 1998; 1998(10): 1105-1107
DOI: 10.1055/s-1998-1886
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Stereoselective Conjugate Addition Directed by an Enantiomerically Pure Ketal. Preparation of the Cyclohexanone Fragment of N-Methylwelwitindolinone C Isothiocyanate

Joseph P. Konopelski* , Hongbo Deng, Kai Schiemann, Joseph M. Keane, Marilyn M. Olmstead
  • *Department of Chemistry and Biochemistry, University of California, Santa Cruz, CA 95064; Fax 408-459-2935; E-mail: joek@chemistry.ucsc.edu
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Publication History

Publication Date:
31 December 2000 (online)

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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.

conjugate addition - chiral ketal - cuprates - marine natural products - alkaloids