Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2012, Issue 27, Pages 5256-5262Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201200599
Keywords
Natural products; Terpenoids; Xiamycin; Atropisomerism; Configuration determination; Density functional calculations
Categories
Funding
- Ministry of Science and Technology of China [2010CB833805, 2012AA092104]
- National Natural Science Foundation of China [31125001, 41006089, 41106143, 40906075]
- Chinese Academy of Sciences [KZCX2-YW-JC202, KSCX2-EW-G-12, 08SL111002]
- [HURO/0901/274/2.2.2]
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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 sp3-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 35.
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