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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Veröffentlicht in:	Chemistry letters 2022-10, Vol.51 (10), p.985-988
Hauptverfasser:	Hirasawa, Shun, Kurashima, Takashi, Hasegawa, Takahiro, Souma, Kazunori, Kanomata, Nobuhiro
Format:	Artikel
Sprache:	eng
Schlagworte:	Aldehydes Crystallization Isocyanates Stereoselectivity Synthesis
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description	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 stereoselective hydration produced the target azaspirene.
doi_str_mv	10.1246/cl.220299
format	Article
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source	Oxford University Press Journals All Titles (1996-Current)
subjects	Aldehydes Crystallization Isocyanates Stereoselectivity Synthesis
title	Total Synthesis of (±)-Azaspirene via Crystallization-induced Diastereomer Transformation
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