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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Bibliographic Details
Published inChemistry letters Vol. 51; no. 10; pp. 985 - 988
Main Authors Hirasawa, Shun, Kurashima, Takashi, Hasegawa, Takahiro, Souma, Kazunori, Kanomata, Nobuhiro
Format Journal Article
LanguageEnglish
Published TOKYO Chemical Soc Japan 05.10.2022
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
Azaspirene
Crystallization-induced diastereomer transformation
(-)-AZASPIRENE
ASYMMETRIC TOTAL-SYNTHESIS
Angiogenic inhibitor
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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.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.220299