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Paper | Regular issue | Vol 98, No. 10, 2019, pp.1384-1407
Published online, 5th November, 2019
DOI: 10.3987/COM-19-14157
Rearrangement Reaction in 1-Hydroxyindole Chemistry: A Synthesis of Novel 7-Substituted Yohimbine, and 4a-Substituted 1,2,3,4-Tetrahydro-β-Carboline DerivaTives1

Katsumasa Yoshino, Fumio Yamada, Koichi Noguchi, Kiyoka Kusuno, and Masanori Somei*

*Noto Marine Laboratory, Institute of Nature and Environmental Technology, Faculty of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, 56-7 Matsuhidai, Matsudo-shi, Chiba 270-2214, Japan

Abstract

X-Ray analyses of 1-hydroxyyohimbine derivatives definitely show the deviation of the N(1)—O bond from the indole molecular plane. This fact supports our working hypothesis “bishomoallylic conjugation”. The deviation is responsible for the rearrangement reaction in 1-hydroxyindole chemistry. Effective synthetic method for novel 7α- and 7β-heteroarylyohimbine, and 4aα- and 4aβ-heteroaryl-1,2,3,4-tetrahydro-β-carboline derivatives are reported.