Total synthesis of (±)-chartelline C

Journal of the American Chemical Society

Volumn 128, Issue 43, 2006, Pages 14028-14029

  Baran, Phil S ^a   Shenvi, Ryan A ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; CHARTELLINE C; UNCLASSIFIED DRUG; CHARTELLINE; INDOLE DERIVATIVE;

ARTICLE; DEPROTECTION REACTION; REACTION ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS; CHEMISTRY; STEREOISOMERISM;

INDOLES; STEREOISOMERISM;

EID: 33750444250     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0659673     Document Type: Article

References (26)

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17. Prepared in four steps (50% yield) from O-TBS D,L-serine methyl ester, see ref 3.
18. Prepared in six steps (44% yield) from 6-bromoindole.
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20. 13C NMR, HMQC, HMBC, HPLC, HRMS, IR, and TLC are included in Supporting Information.
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25. Conformational effects and π-stacking interactions are also believed to contribute significantly to the energetic landscape, as well as to determine the regiochemical outcome of the reaction, that is, which C-2 substituent shifts.
26. For the execution of this rearrangement, see Baran, P. S.; Richter, J. M. J. Am. Chem. Soc. 2005, 127, 15394-15396.