𝔖 Bobbio Scriptorium
✦   LIBER   ✦

A new and efficient approach to the synthesis of nicotine and anabasine analogues

✍ Scribed by Kun Huang; Margarita Ortiz-Marciales; Melvin De Jesús; Viatcheslav Stepanenko

Publisher
Journal of Heterocyclic Chemistry
Year
2009
Tongue
English
Weight
114 KB
Volume
46
Category
Article
ISSN
0022-152X

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

magnified image A straightforward and practical approach was established for the synthesis of nicotine and anabasine analogues by the cyclization of mesylated 1‐(3‐pyridinyl)‐1,4, and 1,5‐diol derivatives to form the pyrrolidino or piperidino fragments. Nicotine analogue (S)‐15 was prepared with good enantioselectivity using the developed azacyclization procedure of nonracemic (R)‐1‐pyridin‐3‐yl‐butane‐1,4‐diol, which was obtained by the borane‐mediated reduction of ketone 12 in the presence of the spiroborate ester derived from diphenyl prolinol and ethylene glycol. J. Heterocyclic Chem., (2009).

📜 SIMILAR VOLUMES

ChemInform Abstract: A Novel Approach to
ChemInform Abstract: A Novel Approach to Conformationally Restricted Analogues of Nicotine and Anabasine by an Intramolecular Hamaguchi—Ibata Reaction.
✍ Tarun K. Sarkar; Sankar Basak; Sunil K. Ghosh 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 30 KB 👁 2 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v

A New Approach to Nicotine: Symmetry Con
A New Approach to Nicotine: Symmetry Consideration for Synthesis Design
✍ Tse-Lok Ho; Eugene V. Kuzakov 📂 Article 📅 2004 🏛 John Wiley and Sons 🌐 German ⚖ 93 KB

## Abstract A synthesis of nicotyrine (**9**), and hence formally racemic nicotine, was carried out by elaboration of the 1 : 1 adduct **2** of cycloocta‐1,5‐diene and chlorosulfonyl isocyanate (ClSO~2~NCO). Transformation of adduct **2** into carbamate **4** was followed by ozonolysis, tosylation