An efficient synthesis of (±)-crinane using an intramolecular azide-olefin cycloaddition

Tetrahedron

Volumn 52, Issue 9, 1996, Pages 3107-3116

  Schkeryantz, Jeffrey M ^a   Pearson, William H ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

1,3 dipolar cycloaddition; alkaloid; azide alkene; crinane; lithium perchlorate; total synthesis

Indexed keywords

CRINANE; INDOLE ALKALOID; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS;

STAPHYLOCOCCUS PHAGE 3A;

EID: 0030068587     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)01098-X     Document Type: Article

References (25)

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2. Review: Martin, S. F. In The Alkaloids; Brossi, A. Ed.; Academic Press: New York; 1987; Vol. 30; pp. 251-376. See also Wildman, W. C. In The Alkaloids; Manske, R. H. F. Ed.; Academic Press: New York; 1960; Vol. 6; p. 289.
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25. Prepared as described by Poon, Y. F.; Thesis dissertation, University of Michigan, 1990, p. 178. A slurry of flash silica gel containing HMDS (20% by weight) was prepared in hexane. The column was wet-packed with this mixture, then eluted consecutively with 50% EtOAc/hex (200 mL), EtOAc (100 mL) and finally the desired solvent system.