A synthetic approach to nomofungin/communesin B

Organic Letters

Volumn 5, Issue 18, 2003, Pages 3169-3171

  Crawley, Seth L ^a   Funk, Raymond L ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COMMUNESIN B; INDOLE; NATURAL PRODUCT; NOMOFUNGIN; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLOADDITION; CYTOTOXICITY; STEREOCHEMISTRY; SYNTHESIS;

ALKALOIDS; CYCLIZATION; EPOXY COMPOUNDS; INDOLEQUINONES; MOLECULAR STRUCTURE;

EID: 0141744761     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034407v     Document Type: Article

References (27)

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2. (b) Erratum: Ratnayake, A. S.; Yoshida, W. Y.; Mooberry, S. L.; Hemscheidt, T. K. J. Org. Chem. 2003, 68, 1640.
3. (a) Numata, A.; Takahashi, C.; Ito, Y.; Takada, T.; Kawai, K.; Usami, Y. ; Matsumura, E.; Imachi, M.; Ito, T.; Hasegawa, T. Tetrahedron Lett. 1993, 34, 2355. Communesin A has an acetamide instead of the sorbamide functionality found in communesin B.
4. (b) For the isolation of a related alkaloid, perophoramidine, which possesses a bis-amidine rather than the bis-aminal functionality present in communesin B, lacks the azepine ring system of communesin B and has a trans-C(7)-C(13) rather than a cis stereochemical relationship, see: Verbitski, S. M.; Mayne, C. L.; Davis, R. A.; Concepcion, G. P.; Ireland, C. M. J. Org. Chem. 2002, 67, 7124.
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10. Both the ester and silyloxymethyl substituents will prefer to emerge on the convex face. The analogous exo transition state has a serious peri interaction between the ester substituent and the proximate aryl ring [calculated ΔE = 2.9 kcal/mol, PC Model, transition state bond order C(7a)-O = 0.4, transition state bond order C(7)-C(13) = 0.2].
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23. 3 The validation of our hypothesis will be the subject of a future communication. For seminal examples of proposed alkaloid biosynthesis (calycanthaceous) originating from tryptamine dimers, see: (a) Robinson, R.; Teuber, H. J. Chem. Ind. 1954, 783. (b) Woodward, R. B.; Yang, N. C.; Katz, T. J. Proc. Chem. Soc. 1960, 76.
24. 3 The validation of our hypothesis will be the subject of a future communication. For seminal examples of proposed alkaloid biosynthesis (calycanthaceous) originating from tryptamine dimers, see: (a) Robinson, R.; Teuber, H. J. Chem. Ind. 1954, 783. (b) Woodward, R. B.; Yang, N. C.; Katz, T. J. Proc. Chem. Soc. 1960, 76.
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27. This relatively mild protocol for generating an aza-ortho-xylylene intermediate is underutilized. For the first and only examples, see: Kubo, H.; Nishiyama, K.; Sato, T.; Higashiyama, K.; Ohmiya, S. Heterocycles 1998, 48, 1103.