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Enantioselective route to ferrugine and its methyl analogue via aldol deoxygenation

✍ Scribed by Michal Sienkiewicz; Urszula Wilkaniec; Ryszard Lazny

Book ID
104097071
Publisher
Elsevier Science
Year
2009
Tongue
French
Weight
264 KB
Volume
50
Category
Article
ISSN
0040-4039

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✦ Synopsis

A simple enantioselective approach to ferrugine (2a-benzoyltropane) and its methyl analogue (2-acetyltropane) is reported. The four-step sequence uses an enantioselective aldol reaction of tropinone with benzaldehyde or acetaldehyde, combined with an aldol deoxygenation via tosylhydrazone reduction and oxidation of the side-chain hydroxy group. The final products, ferrugine and its methyl analogue, are prepared in 35% and 23% overall yields, respectively. Both enantiomers of the products (ee 90-99%) are accessible via the same route using either enantiomer of N,N-bis(1-phenylethyl)amine hydrochloride as the chiral reagent.

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Generation of stannyl derivatives of met
Generation of stannyl derivatives of methyl ketones via a elective silyl/stannyl exchange and its application to aldol reaction
✍ Hirokazu Urabe; Isao Kuwajima 📂 Article 📅 1983 🏛 Elsevier Science 🌐 French ⚖ 199 KB

a-Stannyl derivatives of methyl ketones could be generated from the corresponding silyl enol ethers via a selective silyl/stannyl exchange and were used to prepare aldol products with almost complete regio-and chemo-selectivity. e-Trialkylstannyl ketones and their tautomeric tin enolates are versati