212703-48-5Relevant academic research and scientific papers
A formal synthesis of (+)-discodermolide
Loiseleur, Olivier,Koch, Guido,Cercus, Jacques,Schuerch, Friedrich
, p. 259 - 271 (2005)
Herein, we report the formal synthesis of (+)-discodermolide (1), a promising anticancer agent of sponge origin, in 24 linear steps, with 35 steps in total. The route proceeds from lactone 2, a building block containing the common 1,2-anti-2,3-syn stereot
A practical approach to synthesize the C(9)-C(24) fragment of (+)-discodermolide
Yin, Zengsheng,Yue, Xuyi,Deng, Xiangjun,Qing, Fengling
scheme or table, p. 1400 - 1408 (2010/12/19)
A practical and stereoselective synthesis of the C(9)-C(24) subunit of (+)-discodermolide has been achieved. The strategy featured the construction of the key intermediate Z-trisubstituted vinyl iodide 12 from the dibromoolefin 6 via an efficient modified
Broad spectrum chemistry as practised by Novartis process research
Mickel, Stuart J.,Fischer, Reto,Marterer, Wolfgang
, p. 640 - 648 (2007/10/03)
Three actual examples from the current product palette within Novartis Process Research will demonstrate the some of the variety and challenges encountered in modern chemical development.
Large-Scale Synthesis of the Anti-Cancer Marine Natural Product (+)-Discodermolide. Part 2: Synthesis of Fragments C1-6 and C 9-14
Mickel, Stuart J.,Sedelmeier, Gottfried H.,Niederer, Daniel,Schuerch, Friedrich,Grimler, Dominique,Koch, Guido,Daeffler, Robert,Osmani, Adnan,Hirni, Alfred,Schaer, Karl,Gamboni, Remo,Bach, Andrew,Chaudhary, Apurva,Chen, Stephen,Chen, Weichun,Hu, Bin,Jagoe, Christopher T.,Kim, Hong-Yong,Kinder Jr., Frederick R.,Liu, Yugang,Lu, Yansong,McKenna, Joseph,Prashad, Mahavir,Ramsey, Timothy M.,Repic, Oljan,Rogers, Larry,Shieh, Wen-Chung,Wang, Run-Ming,Waykole, Liladhar
, p. 101 - 106 (2013/09/04)
Kilogram-scale syntheses of fragments C1-6 (6) and C 9-14 (4) of (+)-discodermolide from common precursor 3 are described. Improved procedures for each step of both fragments were developed by minimizing or eliminating the formation
Formal synthesis of (+)-discodermolide.
Francavilla, Charles,Chen, Weichun,Kinder Jr., Frederick R
, p. 1233 - 1236 (2007/10/03)
[structure: see text] Herein we report the formal total synthesis of (+)-discodermolide in 21 steps (longest linear sequence) from commercially available Roche ester. This synthesis features the assembly of C(9-18) and C(19-24) fragments via a metal-chelated aldol coupling reaction.
Evolution of a gram-scale synthesis of (+)-discodermolide
Smith III, Amos B.,Beauchamp, Thomas J.,LaMarche, Matthew J.,Kaufman, Michael D.,Qiu, Yuping,Arimoto, Hirokazu,Jones, David R.,Kobayashi, Kaoru
, p. 8654 - 8664 (2007/10/03)
An efficient, highly convergent, stereocontrolled total synthesis of the potent antimitotic agent (+)-discodermolide (1) has been achieved on gram scale. Key elements of the successful strategy include (1) elaboration of three advanced fragments from a common precursor (CP) which embodies the repeating stereochemical triad of the discodermolide backbone, (2) σr-bond installation of the Z trisubstituted olefin, exploiting a modified Negishi cross-coupling reaction, (3) synthesis of a late-stage phosphonium salt utilizing high pressure, and (4) Wittig installation of the Z disubstituted olefin and the terminal (Z)-diene.
Gram-scale synthesis of (+)-discodermolide.
Smith 3rd.,Kaufman,Beauchamp,LaMarche,Arimoto
, p. 1823 - 1826 (2008/02/11)
[formula: see text] A triply convergent, highly efficient second-generation synthesis of the potent antimitotic agent (+)-discodermolide (1) has been achieved on a 1-g scale.
