Syntheses of CJ-15,161 (1) involving intermolecular N-arylation of an appropriately functionalized diamine, obtained from the precursor alpha-amino acids or, more conveniently, from the corresponding 1,2-amino alcohols via 1,2,3-oxathiazolidine-2,2-dioxide 22, are reported.
View Article and Find Full Text PDFThe architecturally unprecedented sesquiterpene (-)-salsolene oxide (1) has been synthesized in enantioselective fashion from (R)-(-)-carvone. Generation of the phenylthio-substituted vinyl ketene 4 is followed by intramolecular cyclization to the functionalized cyclobutanone 9. Vinyllithium addition to this intermediate proceeds in that stereocontrolled fashion which enables oxy-Cope rearrangement to operate readily under conditions of kinetic control.
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