The intramolecular nitrile oxide cycloaddition (INOC) route to the ergot alkaloids: Use of the isoxazoline to γ-amino alcohol conversion in the total synthesis of (+)-paliclavine

Alan P. Kozikowski, Chen Yon-Yih, Wang B.C, Zhang Bao Xu

Research output: Contribution to journalArticlepeer-review

Abstract

A total synthesis of the ergot alkaloid paliclavine (20), in optically active form is described. The synthesis scheme is based on the intramolecular dipolar cycloaddition reaction of a nitrile oxide to a neighboring olefinic appendage bearing an allylic asymmetric center. The extent of diastereofacial selection in the intramolecular nitrile oxide cycloaddition (INOC) reaction was found to be marginal. A single-crystal X-ray analysis has established the complete stereostructure of the isoxazoline 15 prepared from the "major" INOC product. The dependence of the reduction stereochemistry of the isoxazolinium salt 15a on the nature of the reducing agent is discussed.

Original languageEnglish (US)
Pages (from-to)2345-2358
Number of pages14
JournalTetrahedron
Volume40
Issue number12
DOIs
StatePublished - 1984

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'The intramolecular nitrile oxide cycloaddition (INOC) route to the ergot alkaloids: Use of the isoxazoline to γ-amino alcohol conversion in the total synthesis of (+)-paliclavine'. Together they form a unique fingerprint.

Cite this