Stereoselective Conjugate Addition Directed by an Enantiomerically Pure Ketal. Preparation of the Cyclohexanone Fragment of N-Methylwelwitindolinone C Isothiocyanate

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All articles of this category 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