Total Synthesis of (±)-Azaspirene via Crystallization-induced Diastereomer Transformation

Shun Hirasawa, Takashi Kurashima, Takahiro Hasegawa, Kazunori Souma, Nobuhiro Kanomata*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


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 crystallizationinduced 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.

Original languageEnglish
Pages (from-to)985-988
Number of pages4
JournalChemistry Letters
Issue number10
Publication statusPublished - 2022 Oct


  • Angiogenic inhibitor
  • Azaspirene
  • Crystallization-induced diastereomer transformation

ASJC Scopus subject areas

  • Chemistry(all)


Dive into the research topics of 'Total Synthesis of (±)-Azaspirene via Crystallization-induced Diastereomer Transformation'. Together they form a unique fingerprint.

Cite this