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
DOI:
10.1021/jacs.3c08039
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.
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.
