A concise and stereoselective synthesis of hydroxypyrrolidines: Rapid synthesis of (+)-preussin

Organic Letters

Volumn 12, Issue 18, 2010, Pages 4034-4037

  Draper, Jason A ^a   Britton, Robert ^a  

^a SIMON FRASER UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANISOMYCIN; DRUG DERIVATIVE; PREUSSIN;

ARTICLE; CHEMICAL STRUCTURE; STEREOISOMERISM; SYNTHESIS; TIME;

ANISOMYCIN; MOLECULAR STRUCTURE; STEREOISOMERISM; TIME FACTORS;

EID: 77956564939     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101631e     Document Type: Article

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50. 1H NMR spectral data derived from 5- epi -preussin (17) differed from that reported for this substance in refs 10b and 12f, which were also inconsistent. For characterization purposes, 5- epi- preussin (17) was treated with an excess amount of TFA, which produced a 1:1 mixture of diastereomeric ammonium salts prior to NMR spectroscopic analysis. See the Supporting Information for details.
51. 2 = OTBS) employing the conditions described in entry 6 (Table 1) afforded a 2.3:1 mixture of 3-silyloxypyrrolidines. Treatment of this mixture with TBAF in THF afforded a 2.3:1 mixture of 3: 17.
52. 3).
53. For the preparation, characterization, and stereochemical assignment of all compounds, see the Supporting Information.
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