Concise synthesis of a lactonamycin model system by diastereoselective dihydroxylation of a highly functionalized naphthoquinone

Organic Letters

Volumn 3, Issue 18, 2001, Pages 2899-2902

  Cox, Christopher ^a   Danishefsky, Samuel J ^a,b  

^a Och Spine at New York Presbyterian Hospitals   (United States)

^b MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; INDOLE DERIVATIVE; LACTONAMYCIN; NAPHTHOQUINONE;

ARTICLE; CHEMISTRY; CONFORMATION; HYDROXYLATION; SYNTHESIS;

ANTI-BACTERIAL AGENTS; HYDROXYLATION; INDOLES; MOLECULAR CONFORMATION; NAPHTHOQUINONES;

EID: 0035818013     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016361g     Document Type: Article

References (26)

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19. Also deserving of consideration is a conformer featuring a planar hydrogen bond between the secondary alcohol and the adjacent quinone carbonyl group. In such a reacting ensemble, the phenyl group of the benzyl ether side chain can fold over and engage in a π-stacking interaction with the quinone, successfully explaining the observed stereochemistry. However, two additional considerations do not support this explanation: (1) the proposed hydrogen bond is expected to deactivate the C=C bond toward dihydroxylation and (2) when the hydroxyl group in 13a is protected as a TBS ether, 14a is again obtained with very high stereochemical fidelity (between 8:1 and > 20:1, depending on conditions). A full discussion of the stereochemistry observed in this dihydroxylation will be provided in a forthcoming full paper on the subject.
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