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Synfacts 2023; 19(12): 1173
DOI: 10.1055/s-0043-1772875
Synthesis of Natural Products

Synthesis of (–)-Zygadenine

Contributor(s):
Erick M. Carreira
,
Bilal Kicin
Guo Y, Lu J.-T, Fang R, Jiao Y, Liu J, Luo T. * Peking University, Beijing, P. R. of China
Enantioselective Total Synthesis of (–)-Zygadenine.

J. Am. Chem. Soc. 2023;
145: 20202-20207
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Key words

(–)-zygadenine - Veratrum alkaloid - Pinnick oxidation - Diels–Alder reaction - Barton–McCombie deoxygenation

Significance

Luo and co-workers report the synthesis of (−)-zygadenine. Key to their approach is a stereoselective intramolecular Diels–Alder reaction, followed by a radical cyclization to construct the hexacyclic carbon skeleton.


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Comment

Cyclization precursor F was prepared from commercially available enone A in five steps. Formation of a mixed anhydride with furan I enabled intramolecular Diels–Alder reaction to diketone J. Treatment with AIBN and tributyltin hydride, followed by reduction furnished hexacyclic K.


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Publication History

Article published online:
15 November 2023

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