Total Synthesis, Stereochemical Assignment, and Biological Activity of All Known (-)-Trigonoliimines

Cited 41 time in webofscience Cited 0 time in scopus
  • Hit : 332
  • Download : 0
A full account of our concise and enantioselective total syntheses of all known (-)-trigonoliimine alkaloids is described. Our retrobiosynthetic analysis of these natural products enabled identification of a single bistryptamine precursor as a precursor to all known trigonoliimines through a sequence of transformations involving asymmetric oxidation and reorganization. Our enantioselective syntheses of these alkaloids enabled the revision of the absolute stereochemistry of (-)-trigonoliimines A, B, and C. We report that trigonoliimines A, B, C and structurally related compounds showed weak anticancer activities against HeLa and U-937 cells.
Publisher
AMER CHEMICAL SOC
Issue Date
2014-01
Language
English
Article Type
Article
Keywords

STEREOCONTROLLED TOTAL-SYNTHESIS; CONCISE TOTAL-SYNTHESIS; ENANTIOSELECTIVE EPOXIDATION; OXIDATIVE REARRANGEMENT; ASYMMETRIC EPOXIDATION; STEREOSELECTIVE-SYNTHESIS; BENZANNULATION REACTIONS; (+/-)-TRIGONOLIIMINE C; TRIFLUOROACETIC-ACID; BIOMIMETIC SYNTHESIS

Citation

JOURNAL OF ORGANIC CHEMISTRY, v.79, no.2, pp.473 - 486

ISSN
0022-3263
DOI
10.1021/jo4020358
URI
http://hdl.handle.net/10203/193063
Appears in Collection
CH-Journal Papers(저널논문)
Files in This Item
There are no files associated with this item.
This item is cited by other documents in WoS
⊙ Detail Information in WoSⓡ Click to see webofscience_button
⊙ Cited 41 items in WoS Click to see citing articles in records_button

qr_code

  • mendeley

    citeulike


rss_1.0 rss_2.0 atom_1.0