1204755-29-2Relevant academic research and scientific papers
Enantioselective total synthesis of β-zearalenol from (s)-propylene oxide
Kotla, Ravindar,Murugulla, Adharvana Chari,Ruddarraju, Radhakrishnamraju,Aparna,Donthabakthuni, Shobha,Sridhar, Gattu
, p. 747 - 752 (2018)
The total synthesis of 14-membered resorcylic acid macrolide, β-zearalenol, was accomplished starting from commercially available enantiomerically pure propylene oxide and methyl 2,4-dihydroxy-6-methylbenzoate using Grignard reaction, asymmetric dihydroxy
Stereoselective synthesis of 5′-hydroxyzearalenone
Avuluri, Srilatha,Bujaranipalli, Sheshurao,Das, Saibal,Yadav
, p. 3547 - 3549 (2018/08/29)
A first stereoselective total synthesis of 14-memebered β-resorcylic macrolactone 5′-hydroxyzearalenone (1) has been achieved. The key steps are Jocobsen hydrolytic kinetic resolution, Sharpless asymmetric dihydroxylation, Vilsmeier-Haack reaction, Mitsunobu esterification and ring-closing metathesis.
Total Synthesis and Cytotoxic Activity of 5′-Hydroxyzearalenone and 5′β-Hydroxyzearalenone
Thiraporn, Aticha,Rukachaisirikul, Vatcharin,Iawsipo, Panata,Somwang, Tatiyar,Tadpetch, Kwanruthai
supporting information, p. 7133 - 7147 (2017/12/28)
An efficient and convergent synthesis of 5′-hydroxyzearalenone and 5′β-hydroxyzearalenone, 14-membered β-resorcylic acid lactone (RAL) natural products, has been achieved in a longest linear sequence of 19 steps, and a total of 29 steps, starting from commercially available 5-hexen-1-ol and methyl 2-(3,5-dimethoxyphenyl)acetate. The key features of our synthesis include a Jacobsen hydrolytic kinetic resolution, a Mitsunobu esterification and (an E)-selective ring-closing metathesis (RCM). Our synthesis also highlights the utility of the acetal protecting group for the resorcylate moiety, and its compatibility with RCM reactions for the synthesis of 14-membered RALs. The cytotoxic activity of both synthetic compounds was evaluated against seven human cancer cell lines. 5′-Hydroxyzearalenone shows more potent cytotoxic activity against most of the cancer cell lines tested than its epimer, 5′β-hydroxyzearalenone. Both compounds show significant cytotoxic activity against the C33A cervical cancer cell line, with IC50 values of 21.33 ± 6.43 μm and 16.00 ± 12.17 μm, respectively.
Total synthesis of (3R,5R) and (3R,5S)-sonnerlactones
Sanaboina, Chakrapani,Chidara, Sridhar,Jana, Samaresh,Eppakayala, Laxminarayana
supporting information, p. 1767 - 1770 (2016/04/05)
In this Letter, an enantioselective synthesis of (3R,5R)-sonnerlactone and (3R,5S)-sonnerlactone have been described. Stereochemistry at C-5 position was fixed using a suitable proline catalyzed reaction during the synthesis of aliphatic segment. To accom
Catalytic asymmetric total synthesis of (S)-(-)-zearalenone, a novel lipoxygenase inhibitor
Baggelaar, Marc P.,Huang, Yange,Feringa, Ben L.,Dekker, Frank J.,Minnaard, Adriaan J.
, p. 5271 - 5274 (2013/09/02)
A catalytic asymmetric synthesis of (S)-(-)-zearalenone is reported using asymmetric allylic alkylation for the introduction of the stereocenter. (S)-(-)-Zearalenone turned out to be a novel lipoxygenase inhibitor.
A concise total synthesis of (S)-zearalenone and zeranol
Yadav,Murthy, P. Vishnu
, p. 2117 - 2124 (2011/08/05)
A convergent total synthesis of the naturally occurring, 14-membered macrolides (S)-zearalenone and zeranol has been achieved through application of the Diels-Alder reaction, Jacobsen kinetic resolution, Mitsunobu coupling, ring-closing metathesis, and hy
Access to resorcylic acid lactones via phosphonate based intramolecular olefination
Napolitano, Carmela,McArdle, Patrick,Murphy, Paul V.
supporting information; experimental part, p. 7404 - 7407 (2011/02/22)
An approach to resorcylic acid lactones is described, exploiting an intramolecular olefination reaction for the generation of the 14-membered macrolactone. The synthetic route gave zearalenone precursors, and the preparations of other RAL analogues, trans
