The Synthesis of Desethylibogamine

Abstract

phan residues, it is compelling to consider these two phenomena may be related.In this connection Hayashi, et a/.,12 have shown that a tryptophan residue is involved in the formation of the enzyme-substrate complex between lysozyme and poly-N-acetylglucosamine (glycol chitin). Further, it has been reported by Hartdegen and Rupley13 that an inactive derivative, altered only in a single tryptophan residue, may be obtained by oxidation of lysozyme by iodine in acidic solution. This modification and loss of activity were prevented by the presence of N-acetylglucosamine.Further improvement in instrumentation will be necessary before more accurate measurements of the small aromatic Cotton effects can be obtained. Efforts in this direction are now being made and further results will be published in due course.

A stereochemical controlled total synthesis of DL-ibogamine and DL-epiibogamine

“…The samples of la and lb were proven to be identical with authentic samples of dZ-ibogamine and dZ-epiibogamine (mixture melting point, infrared spectra, and tic). 16 The present synthesis is parallel to our previous skeleton synthesis,4 confirming the correctness of the latter synthesis and of the synthesis reported by Huffman and his coworkers.16 dZ-Ibogamine (la) was directly obtained together with the unstable enamine 16a (R = H instead of OCH3) by diisobutylaluminum hydride reduction of the lactam tosylate 14a. Conversion of this enamine into la is currently being studied.…”

Progress in the Synthesis of Iboga-alkaloids and their Congeners

“…Further synthetic manipulations provided deethylibogamine 42,43 and ibogamine, 44 respectively (Scheme 3). Using a similar approach and at the same time, Kuehne and Reider 45 reported the synthesis of ibogamine via the formation of lactam 69a which was derived from a mixture of the same epoxides, 68.…”

Azepinoindoles. I. Hexahydroazepino[4,5-b]indoles

“…Acknowledgment.-The authors tire indebted to Dr. G. S. 1'onken and his associates for generous supplies of starting material, to Dr. W. A. Struck and his associates for physical and analytical data, and to Mr. D. 11 Hooker, Mr. J. R. Greene, Mr. H. J. Triezenberg, Mr. R. A. Zandt, Mr. A. P. Tazelaar, and Mr. P. Russell for laboratory assistance.…”