146236-73-9Relevant 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.
Highly diastereoselective total syntheses of (+)-7-epigoniodiol, (-)-8-epigoniodiol, and (+)-9-deoxygoniopypyrone
Kumaraswamy, Gullapalli,Satish Kumar, Rangaraju
, p. 1366 - 1375 (2013/08/23)
An expedient concise total synthesis of (+)-7-epigoniodiol, (-)-8-epigoniodiol, and (+)-9-deoxygoniopypyrone is accomplished. The key transformations include a catalytic hydroxylation and base-mediated N-(acetyl)oxazolidinone addition reactions, which cou
Tandem α-aminoxylation-allylation reaction based approach for the synthesis of goniothalesdiol A, leiocarpin A and (+)-goniodiol
Sabitha, Gowravaram,Rammohan Reddy,Yadav
, p. 6550 - 6553 (2012/01/06)
A short and efficient syntheses of goniothalesdiol A, leiocarpin A, and (+)-goniodiol are reported by a convergent strategy using tandem aminoxylation-allylation reaction as a key step starting from benzaldehyde.
An efficient total synthesis of (+)-goniodiol
Sabitha, Gowravaram,Bhikshapathi,Ranjith,Ashwini,Yadav, Jhillu S.
, p. 821 - 825 (2011/04/25)
An efficient total synthesis of (+)-goniodiol was illustrated by using Carreira alkynylation and Sharpless asymmetric dihydroxylation as key steps. Georg Thieme Verlag Stuttgart New York.
A concise enantioselective synthesis of (+)-goniodiol and (+)-8-methoxygoniodiol via Co-catalyzed HKR of anti-(2SR, 3RS)-3-methoxy-3- phenyl-1, 2-epoxypropane
Kiran, I.N. Chaithanya,Reddy, R. Santhosh,Suryavanshi, Gurunath,Sudalai, Arumugam
scheme or table, p. 438 - 440 (2011/03/18)
A short, enantioselective synthesis of (+)-goniodiol and (+)-8-methoxygoniodiol, cytotoxic styryllactones, has been achieved in high optical purities (99% ee). The strategy employs Co-catalyzed HKR of racemic anti-(2SR, 3RS)-3-methoxy-3-phenyl-1, 2-epoxypropane and Lewis acid-mediated diastereoselective allylation of aldehyde as chiral inducing key reactions.
Stereoselective and facile total synthesis of (+)-goniodiol, a styryllactone from carbohydrates
Yadav, Jhillu Singh,Das, Saibal,Mishra, Anand Kumar
experimental part, p. 2443 - 2447 (2011/02/22)
The stereoselective synthesis of (+)-goniodiol, a cytotoxic styryllactone, has been accomplished in 10 steps starting from inexpensive and readily available d-manitol and δ-gluconolactone involving the direct and straightforward reaction conditions of Gri
Stereoselective total synthesis of leiocarpin C and (+)-goniodiol
Yadav,Krishna, V. Hari,Srilatha,Somaiah,Reddy, B. V. Subba
experimental part, p. 3004 - 3012 (2010/10/21)
Total syntheses of styryl lactones, leiocarpin C and (+)-goniodiol have been accomplished in a highly stereoselective manner. The key steps involved in these syntheses are the Chan alkyne reduction, Sharpless asymmetric dihydroxylation, Horner-Wadsworth-E
Stereoselective synthesis of (+)-goniodiol, (+)-goniotriol, (-)-goniofupyrone, and (+)-altholactone using a catalytic asymmetric hetero-Diels-Alder/allylboration approach
Favre, Annaick,Carreaux, Francois,Deligny, Michael,Carboni, Bertrand
experimental part, p. 4900 - 4907 (2009/06/06)
The stereoselective total synthesis of several members of the styryllactone family was achieved efficiently from common intermediate 8, prepared by a catalytic asymmetric inverse-electron-demand hetero-Diels-Alder/allylboration sequence. The transformatio
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.
The first stereoselective and the total synthesis of Leiocarpin C and total synthesis of (+)-Goniodiol
Yadav,Premalatha,Harshavardhan,Subba Reddy
body text, p. 6765 - 6767 (2009/04/11)
The synthesis of the styryl lactone Leiocarpin C has been achieved in a highly stereoselective manner using Jacobsen's kinetic resolution, Sharpless asymmetric epoxidation and Sharpless asymmetric dihydroxylation as key steps. This is the first total synthesis of Leiocarpin C, and thus establishes for the first time the absolute stereochemistry of this natural product.
