156714-47-5Relevant articles and documents
Entecavir intermediate and synthesis method thereof as well as method for synthesis of entecavir
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, (2019/05/15)
The invention relates to an entecavir intermediate and a preparation method thereof and a method for synthesis of entecavir by using the intermediate. The methods for synthesis of the entecavir and the entecavir intermediate have the advantages of controllable chirality, high yield and high product purity, raw materials are wide in source, reagents are cheap and easily available, the reaction is simple, the operation is simple and convenient, green and environment-friendly effects are achieved, and the method is suitable for industrial large-scale production.
Total Synthesis of Entecavir: A Robust Route for Pilot Production
Xu, Hua,Wang, Fang,Xue, Weicai,Zheng, Yunjie,Wang, Qi,Qiu, Fayang G.,Jin, Yehua
, p. 377 - 384 (2018/03/23)
A practical synthetic route for pilot production of entecavir is described. It is safe, robust, and scalable to kilogram scale. Starting from (S)-(+)-carvone, this synthetic route consists of a series of highly efficient reactions including a Favorskii rearrangement-elimination-epimerization sequence to establish the cyclopentene skeleton, the Baeyer-Villiger oxidation/rearrangement to afford the correct configuration of the secondary alcohol, and a directed homoallylic epoxidation followed by epoxide ring-opening to introduce the hydroxyl group suitable for the Mitsunobu reaction. In addition, the synthesis contains only four brief chromatographic purifications.
Study towards diversity oriented synthesis of optically active substituted cyclopentane fused carbocyclic and oxacyclic medium-sized rings: Competition between Grubbs-II catalyzed ring closing olefin metathesis and ring closing carbonyl-olefin metathesis
Chakraborty,Roy
, p. 1831 - 1840 (2016/12/16)
A study towards diversity-oriented synthesis of optically active cyclopentane fused bicyclic frameworks has been accomplished. The common intermediate was prepared from commercially available starting material (S)-carvone. The observations on competition
The search for new odorants: Synthesis of animalic fragrant and musky/ambery compounds
Plessis, Caroline
, p. 1517 - 1539 (2015/03/03)
An overview of the recent research which allowed us to discover novel animalic odorants is presented. The new derivatives were prepared from readily available starting materials via easy reaction steps in good yields. They possess very different structures, such as bicyclic pentanols, glycolates, or tricyclic ketones, and all show interesting notes in the animalic fragrant family: from costus, leathery to ambery and musky scents, making them all attractive for different purposes.
A formal synthesis of iridoid 9-deoxygelsemide
Liu, Yang,Zhao, Gang
, p. 18 - 22 (2013/08/24)
A formal total synthesis of iridoid 9-deoxygelsemide has been accomplished. Our approach features the use of (S)-carvone as starting material, Favorskii rearrangement to construct the functionalized cyclopentane core, Chugeav elimination to introduce the
Concise total synthesis of (-)-8-epigrosheimin
Yang, Haishen,Gao, Yuzhe,Qiao, Xiaoxiao,Xie, Longguan,Xu, Xiaohua
, p. 3670 - 3673 (2011/09/15)
A highly efficient route was developed to synthesize (-)-8-epigrosheimin in four steps from aldehyde 2 based on a substrate-controlled method. The key steps of the synthesis included (1) a stereo- and regioselective allylation addition, (2) an intramolecular translactonization, and (3) an aldehyde-ene cyclization.
Diastereoselective total synthesis of 8-epigrosheimin
Yang, Haishen,Qiao, Xiaoxiao,Li, Fangyi,Ma, Hui,Xie, Longguan,Xu, Xiaohua
supporting information; experimental part, p. 1110 - 1112 (2009/05/27)
The first diastereoselective total synthesis of 8-epigrosheimin was accomplished relying entirely on substrate-controlled methods. 8-Epigrosheimin, isolated as an amoebicidal and antibiotic compound from Crepis virens, is a multi-chiral-centered guaianolide with a cis-hydroazulene and a trans-annulated γ-butyrolactone ring. Our approach featured that the γ-butyrolactone unit was formed firstly before the construction of the cycloheptane ring system. The key steps of the synthesis involved (1) a stereoselective Mukaiyama aldol addition; (2) an oxidative γ-lactonization; and (3) an intramolecular aldehyde-ene cyclization.
Total synthesis of five thapsigargins: Guaianolide natural products exhibiting sub-nanomolar SERCA inhibition
Andrews, Stephen P.,Ball, Matthew,Wierschem, Frank,Cleator, Ed,Oliver, Steven,Hoegenauer, Klemens,Simic, Oliver,Antonello, Alessandra,Huenger, Udo,Smith, Martin D.,Ley, Steven V.
, p. 5688 - 5712 (2008/02/13)
Herein we describe the total synthesis of five guaianolide natural products: thapsigargin. thapsivillosin C, thapsivillosin F, trilobolide and nortrilobolide. Prodrug derivatives of thapsigargin have shown selective in vivo cytotoxicity against prostate tumours and the need for further investigation of this phenomenon highlights the importance of these total syntheses. The first absolute stereochemical assignment of thapsivillosin C is also delineated.
Synthesis of a chiral steroid ring D precursor starting from carvone
Pogrebnoi, Serghei,Sarabèr, Florence C. E.,Jansen, Ben J. M.,De Groot, Aede
, p. 1743 - 1748 (2007/10/03)
A chiral five-membered, silyl enol ether containing, steroid ring D precursor has been synthesized from carvone. This silyl enol ether has been applied in the synthesis of a chiral C17 functionalized steroid skeleton using the addition of a carbocation, g
A Route to the Thapsigargins from (S)-Carvone Providing a Substrate-Controlled Total Synthesis of Trilobolide, Nortrilobolide, and Thapsivillosin F
Oliver, Steven F.,Hoegenauer, Klemens,Simic, Oliver,Antonello, Alessandra,Smith, Martin D.,Ley, Steven V.
, p. 5996 - 6000 (2007/10/03)
An entirely substrate-controlled total synthesis of three members of the thapsigargin family (e.g. trilobolide) is achieved starting from (S)-carvone. The synthesis is linear in nature but is achieved in high yield (> 90% per step). The route permits late
