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Synthesis of Vinca Alkaloids and Related Compounds, XXXVI. A Simple Synthesis of SomeD-Noreburnamenine Derivatives

✍ Scribed by Kalaus, György ;Galambos, János ;Kajtár-Peredy, Mária ;Tamás, JÓZsef ;Szabó, Lajos ;Sápi, János ;Sźantay, Csaba


Publisher
John Wiley and Sons
Year
1987
Tongue
English
Weight
517 KB
Volume
1987
Category
Article
ISSN
0947-3440

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✦ Synopsis


Reaction or the enaminc 5 with u-bromoacryljc esters or achloroacrylonitrilc and subsequent reduction with NaBH4 yielded the pcntacyclic i>-noreburnamenine derivatives 8-10 or I 1 -14. rc-i f k r die Syatbesu voa Vinca-Alkaloiden uod vemandten Vcrbindungen, XXXVI". -Eine eiofacbe Syntbese einiger u-Norcbur-Ramenin-Derivate spcctivcly.


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In the course of an attempted synthesis of E-norvincamine (4) (-)-15-oxovincamone (7), prepared from (-)-vincamone (2), was converted by means of methanolic sodium methoxide to give the (-)-11-cis and (f)-12-trans alcohols. Alkaline hydrolysis of the dioxo compound 7 furnishes the a-0x0 acids 8 and

Synthesis of vinca alkaloids and related
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## Abstract The reaction of the key compound 14 with methyl 4‐formyl‐butanoate (9) or with 5‐benzoyloxypentanal (13) gave the D‐__seco__‐aspidospermane derivatives 17 and 18, respectively. Compound 17 was indirectly and 18 was directly converted to (±)‐20‐deethylvincadifformine (7) and (±)‐20‐deeth