817592-71-5Relevant academic research and scientific papers
Total Synthesis of Gramistilbenoids A, B, and C
Harmalkar, Dipesh S.,Lu, Qili,Lee, Kyeong
, p. 798 - 805 (2018/05/07)
Stilbenes are biologically active metabolites of plants that have the potential to attenuate a broad range of human diseases. Gramistilbenoids are a class of natural products with a stilbene skeleton, isolated from the bamboo orchid (Arundina graminifolia), and with significant cytotoxicity against cancer cell lines (NB4, A549, SHSY5Y, PC3, and MCF7). These are the first identified naturally occurring diphenylethylenes to possess a hydroxyethyl unit. However, some of these compounds are not abundant in nature, and thus, their synthesis is advantageous. This paper reports the first synthesis of gramistilbenoids A (1), B (2), and C (3), with overall yields of 10, 2, and 8% respectively. These natural products were synthesized using key reactions, such as Horner-Wadsworth-Emmons olefination, Stille coupling, and hydroboration-oxidation.
Direct conversion of benzylic and allylic alcohols to phosphonates
Barney, Rocky J.,Richardson, Rebekah M.,Wiemer, David F.
supporting information; experimental part, p. 2875 - 2879 (2011/05/19)
Benzyl phosphonate esters often serve as reagents in Horner-Wadsworth- Emmons reactions. In most cases, they can be prepared from benzylic alcohols via formation of the corresponding halide followed by an Arbuzov reaction. To identify a more direct synthesis of phosphonate esters, we have developed a one-flask procedure for conversion of benzylic and allylic alcohols to the corresponding phosphonates through treatment with triethyl phosphite and ZnI2.
Total synthesis of (+)-machaeriols B and C and of their enantiomers with a cannabinoid structure
Hee, Jin Lee,Yong, Rok Lee,Sung, Hong Kim
experimental part, p. 1404 - 1412 (2009/10/17)
An efficient and concise synthesis of the biologically interesting (+)-machaeriol B (2) and its enantiomer 5 was accomplished from O-phenylhydroxylamine (7) in four steps (Scheme 2). In addition, the first total synthesis of natural (+)-machaeriol C (3) a
Efficient and general preparation of pyranostilbenes: First total synthesis of artocarbene and pawhuskin B
Byung, Ho Park,Yong, Rok Lee,Won, Seok Lyoo
experimental part, p. 2146 - 2154 (2010/02/28)
An efficient and general synthesis providing pyranostilbenes in moderate yields has been developed. It consists of the reaction of pinosylvin with the appropriate a,β-unsaturated aldehyde catalyzed by ethylenediamine diacetate. As an application of this m
Synthesis and structure-activity studies of schweinfurthin B analogs: Evidence for the importance of a D-ring hydrogen bond donor in expression of differential cytotoxicity
Neighbors, Jeffrey D.,Salnikova, Maya S.,Beutler, John A.,Wiemer, David F.
, p. 1771 - 1784 (2007/10/03)
The synthesis and biological evaluation of several enantioenriched schweinfurthin B analogs were undertaken to develop structure-activity relationships and guide design of probes for their putative molecular target. The desired stilbenes contain a common
SCHWEINFURTHIN ANALOGUES
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Page/Page column 42-43, (2010/02/14)
Methods and intermediates for preparing enantiomerically enriched Schweinfurthin analogs which are useful for the treatment of cancer, as well as novel Schweinfurthin analogs having anti-cancer activity, compositions comprising such analogs and therapeuti
