796848-41-4Relevant academic research and scientific papers
Stereoselective Total Synthesis of (+)-Brevipolide H from d -Galactal
Du, Yuguo,Geng, Jialin,Hu, Chao,Liu, Jun,Liu, Yang,Lv, Qingwei,Zhao, Ziyang
, (2022/02/01)
An efficient and concise synthesis of cytotoxic 5,6-dihydro-α-pyrone (+)-brevipolide H has been accomplished in 12 long linear steps in 8.65% overall yield from readily available chiral synthons, D-galactal and ethyl L-lactate. The features of this synthe
Enantioselective synthesis of (+)-brevipolide H
Chen, Ching-Nung,Hou, Duen-Ren
, p. 6762 - 6768 (2016/07/21)
The enantioselective synthesis of natural brevipolide H is reported for the first time. By way of Sharpless epoxidation of penta-1,4-dien-3-ol, both enantiomerically pure epoxides were converted to the corresponding olefins for cross metathesis. Subsequen
Absolute configuration and conformational analysis of brevipolides, bioactive 5,6-dihydro-α-pyrones from Hyptis brevipes
Suárez-Ortiz, G. Alejandra,Cerda-García-Rojas, Carlos M.,Hernández-Rojas, Adriana,Pereda-Miranda, Rogelio
, p. 72 - 78 (2013/03/14)
The (6′S)-configuration of brevipolides A-J (1-10), isolated from Hyptis brevipes, was established by X-ray diffraction analysis of 9 in conjunction with Mosher's ester analysis of the tetrahydro derivative 11 obtained from both geometric isomers 8 and 9 as well as by chemical correlations. The structure of the new brevipolide J (10) was characterized through NMR and MS data as having the same 6-heptyl-5,6-dihydro-2H-pyran-2-one framework possessing the cyclopropane moiety of all brevipolides but substituted by an isoferuloyl group instead of the p-methoxycinnamoyl moiety found in 8 and 9. Conformational analysis of these cytotoxic 6-heptyl-5,6-dihydro-α- pyrones was carried out on compound 9 by application of a protocol based on comparison between experimental and DFT-calculated vicinal 1H- 1H NMR coupling constants. Molecular modeling was used to correlate minimum energy conformers and observed electronic circular dichroism transitions for the isomeric series of brevipolides. Compounds 7-10 exhibited moderate activity (ED50 0.3-8.0 μg/mL) against a variety of tumor cell lines.
