Synthetic Approaches to Fumitremorgins. III. Synthesis of Optically Active Pentacyclic Ring Systems, and Their Oxidation at Ring C
Pictet-Spengler reaction of L-tryptophan methyl ester (9) and 6-methoxy-L-tryptophan methyl ester (40) with isovaleraldehyde (10) in methylene chloride in the presence of trifluoroacetic acid gave the cis-tetrahydro-β-carboline (11, 41) as the major isome
SYNTHETIC APPROACH TO THE TOTAL SYNTHESIS OF FUMITREMORGINS II SYNTHESIS OF OPTICALLY ACTIVE PENTACYCLIC INTERMEDIATES AND THEIR DEHYDROGENATION
Optically active pentacycles ( l3-18 ) were synthesized from L- and D-tryptophans, two of which ( l3 and 15 ) were alkylated and dehydrogenated to 21 and 22, respectively.
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