Synthesis of 1-aza-cryptophycin 1, an unstable cryptophycin. An unusual skeletal rearrangement

Tetrahedron

Volumn 56, Issue 21, 2000, Pages 3339-3351

  Barrow, Russell A ^a   Moore, Richard E ^a   Li, Lian Hai ^a   Tius, Marcus A ^a  

^a UNIVERSITY OF HAWAII   (United States)

Author keywords

Antitumour compounds; Depsipeptides; Natural products; Rearrangements

Indexed keywords

ANTINEOPLASTIC ANTIBIOTIC; CRYPTOPHYCIN 1; CRYPTOPHYCIN DERIVATIVE; DEPSIPEPTIDE; MANDELIC ACID; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034685738     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00255-6     Document Type: Article

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33. 2.
34. The reaction does not proceed in scrupulously anhydrous THF. It is necessary to add a small amount of water to the solvent in order for the reaction to proceed.
35. This compound is not very stable, being prone to cyclise to a THF compound with a trace of base, and is used immediately. If the compound is to be stored, it must be kept in solution at -10°C.
36. This compound it not very stable, being prone to cyclise to a THF compound with a trace of base, and is used immediately. If the compound is to be stored, it should be kept in solution and kept cold.
37. Although 21 could be isolated in an acid/base extraction, the yield was low, which suggests that partitioning between the two phases was incomplete. The use of crude material results in a good overall yield of 23.
38. Air must be rigorously excluded from this reaction.