Total Synthesis of (+/-)-Azaspirene via Crystallization-induced Diastereomer Transformation
The total synthesis of racemic azaspirene was accomplished over 12 steps in a 17% overall yield via a convergent strategy featuring the coupling of isocyanate and 3(2H)-furanone and an intramolecular aldol reaction to construct the spiro core. Later, a complete conversion was achieved via the crysta...
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Published in | Chemistry letters Vol. 51; no. 10; pp. 985 - 988 |
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Main Authors | , , , , |
Format | Journal Article |
Language | English |
Published |
TOKYO
Chemical Soc Japan
05.10.2022
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Subjects | |
Online Access | Get more information |
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Summary: | The total synthesis of racemic azaspirene was accomplished over 12 steps in a 17% overall yield via a convergent strategy featuring the coupling of isocyanate and 3(2H)-furanone and an intramolecular aldol reaction to construct the spiro core. Later, a complete conversion was achieved via the crystallization-induced diastereomer transformation of the kinetically favored epimer-produced primarily via spirocyclic construction-to the thermodynamically stable and desirable epimer. Finally, a stereo selective hydration produced the target azaspirene. |
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ISSN: | 0366-7022 1348-0715 |
DOI: | 10.1246/cl.220299 |