Synthetic approaches to fumitremorgins. III. Synthesis of optically active pentacyclic ring systems, and their oxidation at ring C.

中川昌子， 福島浩， 川手智彦， 本宮光弥…

Index: Nakagawa, Masako; Fukushima, Hiroshi; Kawate, Tomohiko; Hongu, Mitsuya; Une, Teruaki; et al. Chemical and Pharmaceutical Bulletin, 1989 , vol. 37, # 1 p. 23 - 32

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Citation Number: 20

Abstract

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 isomer. The condensation of 11 and 41 with N-benzyloxycarbonyl-L-proline followed by deprotection gave the cis-cis- pentacycles (27, 44) which contain the parent ring system of fumitremorgins. The trans-cis ...