Total synthesis, stereochemical reassignment, and absolute configuration of chlorofusin

Journal of the American Chemical Society

Volumn 129, Issue 32, 2007, Pages 9860-9861

  Sang, Yeul Lee ^a   Clark, Ryan C ^a   Boger, Dale L ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHLOROFUSIN; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; DEPROTECTION REACTION; ENANTIOMER; FUNGUS; MICRODOCHIUM CAESPITOSUM; NUCLEAR MAGNETIC RESONANCE; PROTEIN DEGRADATION; PROTEIN PROTEIN INTERACTION; SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS;

MOLECULAR CONFORMATION; PEPTIDES, CYCLIC; STEREOISOMERISM;

EID: 34547863847     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja073264v     Document Type: Article

References (14)

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2. (b) Duncan, S. J.; Cooper, M. A.; Williams, D. H. Chem. Commun. 2003, 316-317.
3. Boger, D. L.; Desharnais, J.; Capps, K. Angew. Chem., Intl. Ed. 2003, 42, 4138-4176.
4. (a) Desai, P.; Pfeiffer, S. S.; Boger, D. L. Org. Lett. 2003, 5, 5047-5050.
5. For additional preparations of this cyclic peptide, see: (b) Malkinson, J. P.; Zloh, M.; Kadom, M.; Errington, R.; Smith, P. J.; Searcey, M. Org. Lett. 2003, 5, 5051-5054.
6. (c) Tomonori, M.; Miyagi, M.; Suzuki, K.; Shibasaki, M.; Saikawa, Y.; Nakata, M. Heterocycles 2007, 72, 275-291.
7. Qian, W.-J.; Wei, W.-G.; Zhang, Y.-X.; Yao, Z.-J. J. Am. Chem. Soc. 2007, 129, 6400-6401.
8. Chong, R.; King, R. R.; Whalley, W. B. Chem. Commun. 1969, 1512-1513.
9. For additional studies on azaphilones related to the chlorofusin chromophore, see: Zhu, J.; Grigoriadis, N. P.; Lee, J. P.; Porco, J. A., Jr. J. Am. Chem. Soc. 2005, 127, 9342-9343.
10. Wei, W.-G.; Qian, W.-J.; Zhang, Y.-X.; Yao, Z.-J. Tetrahedron Lett. 2006, 47, 4171-4174.
11. (a) Steyn, P. S.; Vleggaar, R. J. Chem. Soc., Perkin Trans. 1 1976, 204-206.
12. (b) Whalley, W. B.; Ferguson, G.; Marsh, W. C.; Restivo, R. J. J. Chem. Soc., Perkin Trans. 1 1976, 1366-1369.
13. These two assignments (δ 115.2 for C2, 101.3 for C6 as reported by Williams) may be switched (δ 101.3 for C2, 115.2 for C6). This tentative reassignment is under continued investigation.
14. 1H NMR spectrum of sufficient quality to confirm that it represents the authentic natural product (see Supporting Information).