474097-60-4Relevant academic research and scientific papers
Biosynthesis-Inspired Total Synthesis of Bioactive Styryllactones (+)-Goniodiol, (6S,7S,8S)-Goniodiol, (-)-Parvistone D, and (+)-Parvistone e
Ramesh, Perla,Rao, Tadikamalla P.
, p. 2060 - 2065 (2016/09/09)
A protecting-group-free total synthesis of (+)-goniodiol (1), (6S,7S,8S)-goniodiol (2), (-)-parvistone D (4), and (+)-parvistone E (6) was efficiently achieved in five steps from commercially available trans-cinnamaldehyde with high overall yields (72-75%). The synthesis strategy was inspired from the proposed biosynthesis pathway of styryllactones. Key transformations of the strategy include a one-pot conversion of goniothalamin oxide to goniodiol or 9-deoxygoniopypyrone in aqueous media, stereoselective epoxidation, ring-closing metathesis, and stereoselective Maruoka allylation. The route is amenable to synthesis of various analogues for biological evaluation.
Syntheses of all stereoisomers of goniodiol from yeast-reduction products and their antimicrobiological activity
Yoshida, Takahiro,Yamauchi, Satoshi,Tago, Ryosuke,Maruyama, Masafumi,Akiyama, Koichi,Sugahara, Takuya,Kishida, Taro,Koba, Yojiro
, p. 2342 - 2352 (2008/12/23)
All stereoisomers of goniodiol were synthesized from yeast-reduction products. The C-6 chiral centers were converted from the chiral centers of the yeast-reduction products. Stereoselective conversion of the alkene, which had been prepared from the yeast-reduction product, to glycol constructed the C-7 and C-8 stereochemistry. (+)-Goniodiol and 7-epi-(+)-goniodiol showed the highest antibacterial activity (MIC, 3.1 mM) against Yersinia intermedia.
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.
Stereoselective synthesis of the styryllactones, 7-epi-goniodiol and leiocarpin A, isolated from Goniothalamus leiocarpus
Chen, Jian,Lin, Guo-Qiang,Liu, Han-Quan
, p. 8111 - 8113 (2007/10/03)
Two novel styryllactones, 7-epi-goniodiol and leiocarpin A, isolated from Goniothalamus leiocarpus, were stereoselectively synthesized in a short and efficient route from cinnamyl alcohol based on the asymmetric epoxidation and the palladium-catalyzed cross-coupling of vinyl epoxide with vinyltributylstannane.
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
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
