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Synfacts 2023; 19(10): 0961
DOI: 10.1055/s-0042-1752780
DOI: 10.1055/s-0042-1752780
Synthesis of Natural Products
Synthesis of (±)-Nominine
Peese KM,
Gin DY.
*
University of Illinois Urbana-Champaign, USA
Efficient Synthetic Access to the Hetisine C20-Diterpenoid Alkaloids. A Concise Synthesis of Nominine via Oxidoisoquinolinium-1,3-Dipolar and Dienamine-Diels–Alder Cycloadditions.
J. Am. Chem. Soc. 2006;
128: 8734-8735
DOI: 10.1021/ja0625430
Efficient Synthetic Access to the Hetisine C20-Diterpenoid Alkaloids. A Concise Synthesis of Nominine via Oxidoisoquinolinium-1,3-Dipolar and Dienamine-Diels–Alder Cycloadditions.
J. Am. Chem. Soc. 2006;
128: 8734-8735
DOI: 10.1021/ja0625430
Key words
(±)-nominine - diterpenoid alkaloid - Wittig reaction - 1,3-dipolar cycloaddition - Birch reduction - Diels–Alder reaction - Riley oxidation
Significance
In 2006, Gin and co-workers reported a total synthesis of the diterpenoid alkaloid (±)‑nominine. Key to their approach is a 1,3-dipolar cycloaddition to construct the pyrrolidine ring and a Diels–Alder reaction to construct the bicyclo[2.2.2]octane of the natural product.
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Comment
The 1,3-dipolar cycloaddition reaction to pyrrolidine K demonstrates a 20% yield due to the emergence of an isomeric side product. This side product can undergo thermal re-equilibration to eventually yield the desired isomer K, thus minimizing loss of material.
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Publication History
Article published online:
14 September 2023
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