872369-17-0Relevant articles and documents
Synthetic studies toward the marine metabolite prorocentin-4: Synthesis of the C1-C23 fragment
Ankireddy, Praveen,Ankireddy, Sandeep,Gowravaram, Sabitha
supporting information, p. 4191 - 4194 (2018/06/12)
A synthetic study of the construction of the C1-C23 fragment of prorocentin-4, a novel linear polyketide, is described. The synthetic highlights include the acid catalyzed epoxide opening, Gilman reaction, Pd(OH)2 catalyzed transformation of a
Synthesis and structure-activity relationship study of FD-891: Importance of the side chain and C8-C9 epoxide for cytotoxic activity against cancer cells
Itagaki, Tomohiro,Kawamata, Ayano,Takeuchi, Miho,Hamada, Keisuke,Iwabuchi, Yoshiharu,Eguchi, Tadashi,Kudo, Fumitaka,Usui, Takeo,Kanoh, Naoki
, p. 287 - 293 (2016/05/09)
Unified synthesis of FD-891 analogs and their structure-activity relationship are described. By using stereoselective allylation/crotylation and Evans aldol chemistry, six side-chain fragments having different length and terminus were synthesized. These f
Synthesis of fully functionalized aglycone of lycoperdinoside A and B
Chandrasekhar, Balla,Athe, Sudhakar,Reddy, P. Purushotham,Ghosh, Subhash
, p. 115 - 124 (2015/02/05)
This article reported the synthesis of fully functionalized aglycone of lycoperdinoside A and B. Pd-catalyzed Stille-Migita cross coupling between E-vinyl iodide 6 and E-vinyl stannane 23 established the highly substituted E,E-diene unit present in lycoperdinoside A and B. The other two Z-olefins present in the molecule were introduced by means of cis-selective Horner-Wadsworth-Emmons reaction with Still-Gennari phosphonate. Evans syn- and anti-aldol reactions were utilized to fix six of the seven stereo centres present in the aglycone. This journal is
Total syntheses of arenamides A, B and C
Chandrasekhar, Srivari,Sathish, Kurapati,Reddy, Gangireddy Pavan Kumar,Mainkar, Prathama S.
, p. 348 - 355 (2014/04/03)
Total syntheses of the three arenamides A-C, NFκB inhibitors, are described for the first time. The key steps involved in the synthesis are a Crimmin's aldol, Wittig olefination and a macrolactamization reaction.
Total syntheses of 28,29-diepi-arenamide A, 29-epi-arenamide A, and 28-epi-arenamide A
Jithender Reddy, V.,Pradhan, Tapan Kumar,Ghosh, Subhash
, p. 6148 - 6150,3 (2020/08/20)
This communication describes the synthesis of stereochemical analogs of arenamide A, a 19-membered cytotoxic depsipeptide isolated from the fermentation broth of a marine bacterial strain Salinispora arenicola. The key steps are diastereoselective aldol r
Total synthesis and stereochemical assignment of (-)-ushikulide A
Trost, Barry M.,O'Boyle, Brendan M.,Hund, Daniel
supporting information; experimental part, p. 15061 - 15074 (2010/01/30)
We report the determination of the full stereostructure of (-)-ushikulide A (1), a spiroketal containing macrolide by total synthesis. Ushikulide A (1) was isolated from a culture broth of Streptomyces sp. IUK-102 and exhibits potent immunosuppressant activity (IC50 = 70 nM). To embark upon an ushikulide A synthesis, a tentative assignment was made based on analogy to cytovaricin (2), a related macrolide isolated from a culture of Streptomyces diastatochromogenes whose full structure was previously established via synthesis and X-ray crystallography. This report delineates studies on several key steps, namely a direct aldol reaction catalyzed by the dinuclear zinc ProPhenol complex, a metal catalyzed spiroketalization, as well as application of an unprecedented asymmetric alkynylation of a simple saturated aldehyde with methyl propiolate to prepare the nucleophilic partner for a Marshall-Tamaru propargylation. These studies culminated in the first total synthesis and stereochemical assignment of (-)-ushikulide A and significantly extended the scope of the above-mentioned methodologies.
The total synthesis and biological properties of the cytotoxic macrolide FD-891 and its non-natural (Z)-C12 isomer
Garcia-Fortanet, Jorge,Murga, Juan,Carda, Miguel,Marco, J. Alberto,Matesanz, Ruth,Diaz, J. Fernando,Barasoain, Isabel
, p. 5060 - 5074 (2008/02/11)
A total, stereoselective synthesis of the naturally occurring, cytotoxic macrolide FD-891 and of its non-natural (Z)-C12 isomer is described. Three fragments of the main carbon chain were stereoselectively prepared by using asymmetric aldol and allylation reactions as the key steps. The molecule was then assembled by using two Julia-Kocienski olefinations to connect the three fragments and a Yamaguchi reaction to close the macrolactone ring. Some specific biological properties (cytotoxicity, binding to tubulin) have been determined for both macrolides. The E configuration of the C12-C13 olefinic bond seems to be an important feature in determining the cytotoxicity but the precise biological mechanism of the latter still remains to be cleared.
Stereoselective synthesis of the cytotoxic macrolide FD-891
Garcia-Fortanet, Jorge,Murga, Juan,Carda, Miguel,Marco, J. Alberto
, p. 2695 - 2698 (2007/10/03)
A total synthesis of the naturally occurring, cytotoxic macrolide FD-891 is described. Three fragments were first stereoselectively constructed using mainly asymmetric aldol and allylation reactions. The complete framework was then assembled using two Jul
Studies toward the total synthesis of tedanolide: stereoselective synthesis of the C(8)-C(17) segment
Nyavanandi, Vijay Kumar,Nanduri, Srinivas,Dev, R. Vasu,Naidu, Andra,Iqbal, Javed
, p. 6667 - 6672 (2007/10/03)
The stereoselective synthesis of the C(8)-C(17) sub-unit (-)-5 of tedanolide (1), which involves iterative Evans aldol reactions as the key steps, is described.
Total synthesis of beauveriolide I
Tian, Hua,Jiao, Xiaozhen,Xie, Ping,Liang, Xiaotian
, p. 8579 - 8581 (2007/10/03)
The first total synthesis of beauveriolide I (1a), a selective ACAT inhibitor, is described. The key steps in this synthesis involved a diastereoselective aldol condensation sequence and a macrocyclization.
