An intramolecular nitrone-olefin dipolar cycloaddition-based approach to total synthesis of the cylindricine and lepadiformine marine alkaloids

Journal of Organic Chemistry

Volumn 64, Issue 13, 1999, Pages 4865-4873

  Werner, Kim M ^a   De Los Santos, Jesus M ^a   Weinreb, Steven M ^a   Shang, Maoyu ^b  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

^b UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 EPI CYLINDRICINE; ALKALOID DERIVATIVE; ALKENE; ALKENE DERIVATIVE; AMINOALCOHOL; CYLINDRICINE; ISOXAZOLIDINE DERIVATIVE; KETONE; LEPADIFORMINE; NITRO DERIVATIVE; OXIME; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; MOLECULAR DYNAMICS; OXIDATION; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0033603519     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990266s     Document Type: Article

References (42)

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40. There seems to be little reason to farther optimize the deoxygenation of ketone 52 since our synthetic compound 60 does not correspond to natural lepadiformine.
41. We thank Professor J. F. Biard for the proton and carbon NMR spectra, as well as a sample of lepadiformine.
42. We appreciate frequent helpful discussions and exchanges of information with Professor William H. Pearson.