Total synthesis of the putative structure of lucentamycin A

Organic Letters

Volumn 11, Issue 22, 2009, Pages 5298-5301

  Pal, Ujjwal ^a   Ranatunga, Sujeewa ^b   Ariyarathna, Yamuna ^b   Del Valle, Juan R ^a  

^a H LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE   (United States)

^b NEW MEXICO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; LUCENTAMYCIN A; OLIGOPEPTIDE;

ARTICLE; CELL PROLIFERATION; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; DRUG SCREENING; HUMAN; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL LINE; X RAY CRYSTALLOGRAPHY;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; CRYSTALLOGRAPHY, X-RAY; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; OLIGOPEPTIDES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 70749111869     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol902251c     Document Type: Article

References (32)

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30. 2-OH resulted in moderate yields of coupled product and significant racemization of the Har residue.
31. Semi-preparative RP-HPLC in the presence and absence of formic acid as an aqueous additive gave products with identical spectroscopic properties. We presume that purified 1 exists in the neutral zwitterionic form.
32. Although an authentic sample of lucentamycin A was unavailable for HPLC co-injection studies, analysis of original NMR data files graciously provided by Prof. Fenical clearly show chemical shift discrepancies. Superimposed NMR expansions are included in the Supporting Information.