Concise total synthesis of (±)-salinosporamide A, (±)-cinnabaramide A, and derivatives via a bis-cyclization process: Implications for a biosynthetic pathway?

Organic Letters

Volumn 9, Issue 11, 2007, Pages 2143-2146

  Gil, Ma ^a   Henry, Nguyen ^a   Romo, Daniel ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CINNABARAMIDE A; LACTONE; PYRROLE DERIVATIVE; SALINOSPORAMIDE A; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; COLOR; SYNTHESIS;

COLOR; LACTONES; MOLECULAR STRUCTURE; PYRROLES;

EID: 34250636718     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070616u     Document Type: Article

References (42)

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42. Yields in this two-step process are lower due to incomplete oxidation and inability to purify the aldehyde due to some sensitivity of this intermediate. Diastereoselectivity is considerably lower than that reported previously (see refs 4a-c); however, this appears to be highly substrate dependent given that Danishefsky observed reduced diastereoselectivity with N-unprotected substrates (ref 4c).