Synthesis of the celogentin C right-hand ring

Organic Letters

Volumn 8, Issue 6, 2006, Pages 1165-1168

  He, Liwen ^a   Yang, Liping ^a   Castle, Steven L ^a  

^a Brigham Young University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CELOGENTIN C; CYCLOPEPTIDE; TUBULIN MODULATOR;

ARTICLE; CELOSIA; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

CELOSIA; MOLECULAR STRUCTURE; PEPTIDES, CYCLIC; TUBULIN MODULATORS;

EID: 33646453051     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060016f     Document Type: Article

References (22)

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17. 3CN, < 10%; DMF, no product observed.
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19. Gibson, F. S.; Bergmeier, S. C.; Rapoport, H. J. Org. Chem. 1994, 59, 3216. The tert-butylating reagent used herein, N,N-diisopropyl-O-tert- butylisourea, is difficult to prepare due to the requirement for strictly anhydrous t-BuOH. Accordingly, we developed a more convenient preparation of 6 which is given in Supporting Information.
20. For a review of peptide coupling reagents, see: Albericio, F.; Chinchilla, R.; Dodsworth, D. J.; Najera, C. Org. Prep. Proced. Int. 2001, 33, 203.
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22. NAr-type reaction employed by Moody to fashion the analogous linkage in the synthesis of the moroidin right-hand ring (see ref 7a) required both strong base (NaHMDS) and heat. Consequently, this transformation, although high-yielding (89%), was performed with relatively simple compounds that were later elaborated into amino acids and peptides.