Formal synthesis of (+)-lactacystin based on a novel radical cyclisation of an α-ethynyl substituted serine

Tetrahedron Letters

Volumn 44, Issue 49, 2003, Pages 8757-8760

  Brennan, Christopher J ^a   Pattenden, Gerald ^a   Rescourio, Gwenaëlla ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AMINOALCOHOL; LACTACYSTIN; PYRROLIDINE DERIVATIVE; SERINE DERIVATIVE;

ARTICLE; CHEMICAL BOND; CYCLIZATION; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOSELECTIVITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; STEREOCHEMISTRY;

EID: 0242298263     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.10.022     Document Type: Article

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36. 2) ppm.
37. C (125 MHz) 173.5 (s), 171.6 (s), 159.5 (s), 129.7 (s), 129.5 (2d), 114.6 (2d), 76.7 (d), 72.4 (s), 62.5 (t), 55.4 (q), 53.4 (s), 52.9 (q), 44.8 (t), 22.9 (q), 12.4 (q) ppm. The stereochemistry was confirmed by selective NOE enhancements.
38. In contemporaneous studies we also examined the radical cyclisation of the ethynyl bromoamide 16 containing additional substitution by an iso-propyl, with the idea of securing a concise synthesis of a more advanced precursor to 14 , i.e. 17 . However, this particular reaction failed and instead led to the product of reduction of the C-Br bond in 16 , possible as a result of facile intramolecular 1,6- or 1,5-H abstraction from the 2-methylpropanol unit in the substrate.