STEREOSELECTIVE CONJUGATE ADDITION DIRECTED BY AN ENANTIOMERICALLY PURE KETAL - PREPARATION OF THE CYCLOHEXANONE FRAGMENT OF N-METHYLWELWITINDOLINONE-C-ISOTHIACYANATE

Authors
KONOPELSKI JP DENG HB SCHIEMANN K KEANE JM OLMSTEAD MM
Citation
Jp. Konopelski et al., STEREOSELECTIVE CONJUGATE ADDITION DIRECTED BY AN ENANTIOMERICALLY PURE KETAL - PREPARATION OF THE CYCLOHEXANONE FRAGMENT OF N-METHYLWELWITINDOLINONE-C-ISOTHIACYANATE, Synlett, (10), 1998, pp. 1105
Citations number
24
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
10
Year of publication
1998
Database
ISI
SICI code
0936-5214(1998):10<1105:SCADBA>2.0.ZU;2-P
Abstract
A cyclohexanone intermediate to be employed in the synthesis of the ma rine natural product N-methylwelwitindolinone C isothiocyanate has bee n 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 cr ystal X-ray analysis of a derivative of the final product established the absolute stereochemistry at C12.