@article{oai:kanazawa-u.repo.nii.ac.jp:00015365, author = {Yoshino, Katsumasa and Yamada, Fumio and Somei, Masanori}, issue = {2}, journal = {Heterocycles}, month = {Nov}, note = {X-Ray analyses of 1-hydroxyyohimbine derivatives clearly show the deviation of the N(1)-O bond from the indole molecular plane. This phenomenon supports our working hypothesis "bishomoallylic conjugation". The deviation is responsible for the unprecedented nucleophilic substitution reaction in 1-hydroxyindole chemistry and effected the synthesis of novel 7β-heteroarylyohimbine and 4aα-heteroaryl-1,2,3,4-tetrahydro-β-carboline derivatives from the corresponding 1-hydroxyindole derivatives. © 2008 The Japan Institute of Heterocyclic Chemistry All rights reserved., 金沢大学医薬保健研究域薬学系, 金沢大学名誉教授}, pages = {989--994}, title = {Nucleophilic substitution reaction in indole chemistry: A synthesis of novel 7β-substituted yohimbine and 4aα-substituted 1,2,3,4-tetrahydro-β-carboline derivatives}, volume = {76}, year = {2008} }