Enantioselective Total Synthesis of (−)-Zygadenine

The Veratrum alkaloids are highly complex steroidal alkaloids characterized by their intricate structural and stereochemical features and exhibit a diverse range of pharmacological activities. A new synthetic pathway has been developed to access this family of natural products, which enabled the fir...

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Published inJournal of the American Chemical Society Vol. 145; no. 37; pp. 20202 - 20207
Main Authors Guo, Yinliang, Lu, Jia-Tian, Fang, Runting, Jiao, Yang, Liu, Jiaqi, Luo, Tuoping
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.09.2023
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
VERATRUM ALKALOID SERIES
BATRACHOTOXIN
ASYMMETRIC-SYNTHESIS
STEROIDS
SEX-HORMONES
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Summary:The Veratrum alkaloids are highly complex steroidal alkaloids characterized by their intricate structural and stereochemical features and exhibit a diverse range of pharmacological activities. A new synthetic pathway has been developed to access this family of natural products, which enabled the first total synthesis of (−)-zygadenine. This synthetic route entails the construction of a hexacyclic carbon skeleton through a stereoselective intramolecular Diels–Alder reaction, followed by a radical cyclization. Subsequently, a meticulously designed sequence of redox manipulations was optimized to achieve the de novo synthesis of this highly oxidized Veratrum alkaloid.
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ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.3c08039