General approach for the synthesis of sarpagine/macroline indole alkaloids. Enantiospecific total synthesis of the indole alkaloid trinervine.
[structure: see text] The total synthesis of the indole alkaloid trinervine 1 was accomplished in enantiospecific fashion in an overall yield of 20% (from the tetracyclic ketone 8) in 10 reaction vessels (12.5% from tryptophan methyl ester). The synthesis of the N(a)-H substituted macroline equivalent 2 was also completed in high yield via the same intermediate 13. The unique protection/hydroboration process developed here should provide a method to functionalize the C(19)-C(20) double bond in similar systems.
Liu
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Department of Chemistry, University of Wisconsin-Milwaukee, Milwaukee, Wisconsin 53201, USA.
Cook
J M
JM
D000818:Animals; D000962:Antimalarials / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D004351:Drug Resistance; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D019684:Magnoliopsida / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D010963:Plasmodium falciparum / Q000187:drug effects; D013237:Stereoisomerism
D000962:Antimalarials; D026121:Indole Alkaloids; D007211:Indoles; C447980:trinervine