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N–N‐Coupled Indolo‐sesquiterpene Atropo‐Diastereomers from a Marine‐Derived Actinomycete
Open accessAbstract
Four new indolo‐sesquiterpenes – dixiamycins A (1) and B (2), oxiamycin (3), and chloroxiamycin (4) – were isolated from a marine‐derived Actinomycete and characterized, together with the known compound xiamycin A (5). Dixiamycins A (1) and B (2) are the first examples of atropisomerism of naturally occurring N‐N‐coupled atropo‐diastereomers, with a dimeric indolo‐sesquiterpene skeleton and a stereogenic N‐N axis between sp 3‐hybridized nitrogen atoms. Solution TDDFT ECD calculations were utilized to ascertain the axial chirality of 1 and 2, and rotational barriers and transitions states of the inversion were calculated. Oxiamycin (3) contains a seven‐membered 2,3,4,5‐tetrahydrooxepine ring. The two dimeric compounds 1 and 2 showed better antibacterial activities than the monomers 3–5.
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Cited by
Faulkner, D. J. (1990) · Natural Product Reports · doi:10.1039/np9900700269 · Cited by 4,866
Renaissance of Electrosynthetic Methods for the Construction of Complex Molecules
Waldvogel, S. R., & Janza, B. (2014) · Angewandte Chemie International Edition · doi:10.1002/anie.201405082 · Cited by 271
Current Status and Future Prospects of Marine Natural Products (MNPs) as Antimicrobials
Choudhary, A., Naughton, L., Montánchez, I., Dobson, A., & Rai, D. (2017) · Marine Drugs · doi:10.3390/md15090272 · Cited by 138
Metadata
- Authors
- Zhang, Q., Mándi, A., Li, S., Chen, Y., Zhang, W., Tian, X., Zhang, H., Li, H., Zhang, W., Zhang, S., Ju, J., Kurtán, T., & Zhang, C.
- Venue
- European Journal of Organic Chemistry
- Publisher
- Wiley
- Published
- 2012-08-13
- Volume
- 2012
- Issue
- 27
- Pages
- 5256-5262
- ISSN
- 1099-0690 (ISSN-L)
- 1434-193X
- OpenAlex
- W2041529108
- Cited by
- 183
- References
- 0
- FWCI
- 6.19
- Type
- journal article
- Language
- en
- Open access
- green
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- Zhang, Q., Mándi, A., Li, S., Chen, Y., Zhang, W., Tian, X., Zhang, H., Li, H., Zhang, W., Zhang, S., Ju, J., Kurtán, T., & Zhang, C. (2012). N–N‐Coupled Indolo‐sesquiterpene Atropo‐Diastereomers from a Marine‐Derived Actinomycete. European Journal of Organic Chemistry. https://doi.org/10.1002/ejoc.201200599
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