2010 journal article

A Five-Step Synthesis of (S)-Macrostomine from (S)-Nicotine

ORGANIC LETTERS, 12(20), 4513–4515.

By: M. Enamorado n, P. Ondachi n & D. Comins n

MeSH headings : Isoquinolines / chemical synthesis; Molecular Structure; Nicotine / chemistry
TL;DR: A concise synthesis of (S)-macrostomine has been accomplished in five steps from natural nicotine in 19% overall yield via a pyridyne Diels-Alder cycloaddition reaction as the key step. (via Semantic Scholar)
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Added: August 6, 2018

2010 journal article

Synthesis of Fused-Ring Nicotine Derivatives from (S)-Nicotine

JOURNAL OF ORGANIC CHEMISTRY, 75(5), 1706–1716.

By: P. Ondachi n & D. Comins n

MeSH headings : Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis; Bridged Bicyclo Compounds, Heterocyclic / chemistry; Cyclization; Dioxins / chemical synthesis; Dioxins / chemistry; Magnetic Resonance Spectroscopy; Mass Spectrometry; Molecular Structure; Nicotine / chemical synthesis; Nicotine / chemistry; Stereoisomerism
TL;DR: The synthesis of novel fused-ring bicyclic and tricyclic nicotine derivatives from natural (S)-nicotine are described and attempts to synthesize furonicotines resulted in formation of the furonicotine dimers 42 and 49. (via Semantic Scholar)
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2007 journal article

Synthesis and regioselective substitution of C-6 alkoxy derivatives of (S)-nicotine

TETRAHEDRON LETTERS, 49(3), 569–572.

By: P. Ondachi n & D. Comins n

author keywords: (S)-nicotine; alkoxynicotine; lithiation; regioselective deprotonation
TL;DR: Enantiopure (S)-6-alkoxynicotine derivatives have been synthesized in two steps from (S-nicotine via (S)"6-iodonicotine", using mesityllithium as the base at 0 °C fordeprotonation and substitution at the C-5 position of the pyridine ring of (S)+6-methoxynICotine. (via Semantic Scholar)
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Added: August 6, 2018

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