Studies directed toward the synthesis of the guanidine alkaloid, spiroleucettadine: Some observations at the level of structure

Tetrahedron Letters

Volumn 47, Issue 3, 2006, Pages 385-387

  Li, Chaomin ^a   Danishefsky, Samuel J ^a,b  

^a Och Spine at New York Presbyterian Hospitals   (United States)

^b MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID DERIVATIVE; SPIROLEUCETTADINE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; STRUCTURE ANALYSIS;

EID: 28844443802     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.11.002     Document Type: Article

References (10)

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4. Because both Z and E olefin isomers are transformed into the same product (9 ) at the olefin hydrogenation step, the two isomers were carried through the next two steps without separation. For the assignment of the Z and E stereochemistry, see: D. Villemin, and B. Martin Synth. Commun. 25 1995 3135
5. G.L. Kenyon, and G.L. Rowley J. Am. Chem. Soc. 93 1971 5552 and references cited therein
6. We also note that when the non-Boc-protected congener of 11 was subjected to the oxidation conditions, the analogous quinol intermediate was observed, in 21% yield.
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10. On the basis of NMR analysis, 24 exists as a 1.8:1 isomeric mixture of products, which are inseparable by silica gel column chromatography.