Synthetic application of acylnitroso Diels-Alder derived aminocyclopentenols: total synthesis of (+)-streptazolin

Fangzheng Li; Namal C Warshakoon; Marvin J Miller

doi:10.1021/jo048606j

Synthetic application of acylnitroso Diels-Alder derived aminocyclopentenols: total synthesis of (+)-streptazolin

J Org Chem. 2004 Dec 10;69(25):8836-41. doi: 10.1021/jo048606j.

Authors

Fangzheng Li¹, Namal C Warshakoon, Marvin J Miller

Affiliation

¹ Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556, USA.

PMID: 15575765
DOI: 10.1021/jo048606j

Abstract

Concise total syntheses of (+)-streptazolin 1 and its more stable dihydro derivative 2 were accomplished via an intramolecular aldol condensation strategy starting from readily available aminocyclopentenol (-)-7. The synthetic sequence included reductive amination, stereoselective epoxidation, intramolecular aldol (and condensation) reaction, and Wittig reaction. The overall yield for dihydro derivative 2 from aminocyclopentenol (-)-7 was about 7% for a total of 14 steps.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, P.H.S.

MeSH terms

Acylation
Cyclopentanes / chemistry
Molecular Conformation
Nitroso Compounds / chemistry*
Piperidines / chemical synthesis*
Stereoisomerism

Substances

Cyclopentanes
Nitroso Compounds
Piperidines
streptazolin