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Zenichi Yoshida (1925-2023)
Zenichi Yoshida (1925-2023)
Professor. Zenichi Yoshida,
a member of the Honorary Advisors of HETEROCYCLES (1975-1998),
has passed away on May 4, 2023 at the age of 97.
I deeply express my regret over his death.
Kunio Ogasawara
Editor
May 11, 2023
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Paper | Regular issue | Vol 27, No. 7, 1988, pp.1709-1712
Published online, 1st January, 1970■ Improvements in the Total Synthesis of Physostigmine: Reductive Cyclization of Oxindoles to Tricyclic Indoleninepyrrolidines with Lithium Aluminium Hydride in Tetrahysrofuran
Published online, 1st January, 1970
DOI: 10.3987/COM-88-4569
■ Improvements in the Total Synthesis of Physostigmine: Reductive Cyclization of Oxindoles to Tricyclic Indoleninepyrrolidines with Lithium Aluminium Hydride in Tetrahysrofuran
Qian-Sheng Yu and Arnold Brossi*
*Medical Chemistry Section, Laboratory of Chemistry, NIDDK,. National Institute of Health, Bethesda, MD 20892, U.S.A.
Abstract
Reductive cyclization of oxindole 2 and carbamate 5 with LAH in THF afforded the indoleninepyrrolidines 7 and 11 in high yield. The former compound is an important intermediate in our syntheeia of (-)- and (+)-physostigmine (optical isomers of 12). Menthylearbamatee 6 and 9 prepared from 4 and 7 with menthyl chloroformate could not be separated respectively on TCL by standard techniques.
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