On the fate of the tryptophan stereocenter during the synthesis of hexacyclic analogues of N-acetylardeemin

Tetrahedron Asymmetry

Volumn 9, Issue 17, 1998, Pages 3025-3038

  Caballero, Esmeralda ^a   Avendaño, Carmen ^a   Menéndez, J Carlos ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALANINE; FISCALIN B; FUMIQUINAZOLINE A; N ACETYLARDEEMIN; N ACETYLARDEEMIN DERIVATIVE; NATURAL PRODUCT; TRYPTOPHAN; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CHEMICAL STRUCTURE; MOLECULAR DYNAMICS; MULTIDRUG RESISTANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0032483434     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00307-3     Document Type: Article

References (27)

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23. Otherwise, they revert easily to the starting diketopiperazines.
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25. 8=O groups, although not as efficiently as epimerization at the tryptophan stereocenter.
26. This behavior is similar to the one found by Rajappa and Advani for a similar reaction of cyclo-(L-Pro-L-Val), although they do not give the actual yields of both stereoisomers. See Ref 6a.
27. Compounds 11 and 15 were initially recovered as a mixture with compounds 1c and 1f, respectively, arising from the hydrolysis of the starting iminoethers. Their chromatographic separation was not possible, and therefore the mixture was treated with triethyloxonium tetrafluoroborate to transform 1c and 1f into 9 and 14, respectively, which allowed the purification of the hexacyclic compounds 11 and 15.