130718-77-3Relevant academic research and scientific papers
Total synthesis and cytotoxicity of (+)- and (-)-goniodiol and 6-epi-goniodiol. Construction of α,β-unsaturated lactones by ring-closing metathesis
Nakashima, Katsuyuki,Kikuchi, Naoki,Shirayama, Daisuke,Miki, Takuo,Ando, Kazuhiro,Sono, Masakazu,Suzuki, Shinya,Kawase, Masaki,Kondoh, Masuo,Sato, Masao,Tori, Motoo
, p. 387 - 394 (2008/02/11)
(+)-Goniodiol, a potent and selective cytotoxin, and (-)-6-epi-goniodiol, as well as their enantiomers, have been synthesized starting from cinnamyl alcohol. The key steps of the synthesis were Sharpless asymmetric epoxidation and cyclization of an acrylate derivative using ring-closing metathesis reaction. The cytotoxicity of both enantiomers of goniodiol and 6-epi-goniodiol against HL-60 cells was examined.
A total synthesis of the styryllactone (+)-goniodiol from naphthalene
Banwell, Martin G.,Coster, Mark J.,Edwards, Alison J.,Karunaratne, Ochitha P.,Smith, Jason A.,Welling, Lee L.,Willis, Anthony C.
, p. 585 - 595 (2007/10/03)
The cytotoxic natural product (+)-goniodiol (1) has been prepared in twelve steps from the enantiomerically pure cis-dihydrocatechol (2), which is readily obtained by microbial oxidation of naphthalene. Elaboration of compound (2) involves an initial oxid
Stereoselective syntheses of (+)-goniodiol, (-)-8-epigoniodiol, and (+)-9-deoxygoniopypyrone via alkoxyallylboration and ring-closing metathesis
Ramachandran, P. Veeraraghavan,Chandra, J. Subash,Reddy, M. Venkat Ram
, p. 7547 - 7550 (2007/10/03)
A convenient synthesis of (+)-goniodiol, (-)-8-epigoniodiol, and (+)-9-deoxygoniopypyrone has been developed via asymmetric alkoxyallylboration and ring-closing metathesis pathways.
A chemoenzymatic synthesis of the styryllactone (+)-goniodiol from naphthalene
Banwell, Martin G.,Coster, Mark J.,Karunaratne, Ochitha P.,Smith, Jason A.
, p. 1622 - 1624 (2007/10/03)
The enantiomerically pure cis-1,2-diol 2, which is obtained by microbial oxidation of naphthalene, has been converted, via a sequence of reactions including oxidative C-C bond cleavage, decarbonylation and ring-closing metathesis steps, into the natural p
Asymmetric Total Synthesis of (+)-Goniotriol and (+)-Goniofufurone
Yang, Zhi-cai,Zhou, Wei-shan
, p. 1429 - 1436 (2007/10/02)
Thr Enantioselective synthesis of two antitumor styryl lactones, (+)-goniotriol and (+)-goniofufurone, have been completed starting from cinnamyl alcohol in ten and eleven steps with an overall yield of 21percent and 12percent, respectively.
Total synthesis of the natural goniodiol-8-monoacetate from cinnamyl alcohol
Yang,Zhou
, p. 743 - 744 (2007/10/02)
The first total synthesis of goniodiol-8-monoacetate, using the Sharpless asymmetric epoxidation starting from cinnamyl alcohol in twelve steps with an overall yield of 7%, is achieved.
Synthesis of O-Protected (R)-2-Hydroxy Aldehyde and Their Hydrocyanation
Effenberger, Franz,Hopf, Martin,Ziegler, Thomas,Hudelmayer, Jochen
, p. 1651 - 1659 (2007/10/02)
The synthesis of O-silyl- and O-benzyl-protected (R)-2-hydroxy aldehydes (R)-6 from (R)-2-hydroxy carboxylic acids (R)-1 is described.While attempts for their diastereoselective hydrocyanation with hydrocyanic acid and (R)-oxynitrilase as catalyst have not been successful, the cyano silylation with trimethylsilyl cyanide occurred diastereoselectively with a ratio of 81:19 preferring the threo form without racemization at C-2 of the 2-hydroxy aldehyde. Key Words : (R)-2-Hydroxy aldehydes, O-protected / Hydrocyanation
Synthesis of Aryl Carbohydrate Synthons and 2,3-Dihydroxypropanoic Acid Derivatives of High Optical Purity
Matthews, Barry R.,Jackson, W. Roy,Jacobs, Howard A.,Watson, Keith G.
, p. 1195 - 1214 (2007/10/02)
General routes to bith L and D aryl carbohydrate precursors and to erythro and threo 2,3-dihydroxypropanoic acid of high optical purity have been established from readily available optically active aryl cyanohydrins.
