Tandem organocatalytic approach to C28–C35 fragment of eribulin mesylate

作者: Lahu N. Chavan , Rambabu Chegondi , Srivari Chandrasekhar

DOI: 10.1016/J.TETLET.2015.05.075

关键词: Total synthesisStereochemistryFragment (logic)TandemEribulin MesylateAnticancer drugChemistry

摘要: The organocatalytic approach is devised for the synthesis of C28–C35 fragment anticancer drug eribulin mesylate (Halaven®) amenable scaleup toward total synthesis.

参考文章(18)
Hiroyuki Chiba, Katsuya Tagami, ハラヴェン(エリブリンメシル酸塩)の開発研究 Journal of Synthetic Organic Chemistry Japan. ,vol. 69, pp. 600- 610 ,(2011) , 10.5059/YUKIGOSEIKYOKAISHI.69.600
Akondi Srirama Murthy, Srivari Chandrasekhar, Practical and stereoselective synthesis of [6,6,5]-tricyclic core (C1–C13) of eribulin mesylate Tetrahedron Letters. ,vol. 56, pp. 4280- 4282 ,(2015) , 10.1016/J.TETLET.2015.05.074
Nadella Lavanya, Nayani Kiranmai, Prathama S. Mainkar, Srivari Chandrasekhar, A practical synthesis of C14–C26 fragment of anticancer drug, eribulin mesylate Tetrahedron Letters. ,vol. 56, pp. 4283- 4285 ,(2015) , 10.1016/J.TETLET.2015.05.077
Boris M. Seletsky, Kimberley K. Aalfs, Kathleen A. Salvato, Kentaro Yoshimatsu, Lucian V. DiPietro, Bruce F. Wels, Gregory J. Habgood, Murray J. Towle, Monica H. Palme, Lori A. Singer, Melvin J. Yu, Yoshito Kishi, Jacqueline Budrow, Galina Kuznetsov, Ashley Davis, Jack J. Chen, Yuan Wang, David A. Quincy, Susan Welsh, Bruce A. Littlefield, Wanjun Zheng, In vitro and in vivo anticancer activities of synthetic macrocyclic ketone analogues of halichondrin B Cancer Research. ,vol. 61, pp. 1013- 1021 ,(2001)
Takasuke Mukaiyama, Hayato Ishikawa, Hiroyuki Koshino, Yujiro Hayashi, One-pot synthesis of (-)-oseltamivir and mechanistic insights into the organocatalyzed Michael reaction Chemistry: A European Journal. ,vol. 19, pp. 17789- 17800 ,(2013) , 10.1002/CHEM.201302371
Jeffrey A. Dodge, John I. Trujillo, Misti Presnell, Effect of the acidic component on the Mitsunobu inversion of a sterically hindered alcohol Journal of Organic Chemistry. ,vol. 59, pp. 234- 236 ,(1994) , 10.1021/JO00080A039
Akondi Srirama Murthy, Bodugum Mahipal, Srivari Chandrasekhar, Asymmetric Synthesis of the C14–C26 Building Block of Eribulin Mesylate European Journal of Organic Chemistry. ,vol. 2012, pp. 6959- 6966 ,(2012) , 10.1002/EJOC.201201119
Ravikumar Jimmidi, Shiva Krishna Reddy Guduru, Prabhat Arya, Practical Stereoselective Synthesis of Eribulin Fragment toward Building a Hybrid Macrocyclic Toolbox Organic Letters. ,vol. 17, pp. 468- 471 ,(2015) , 10.1021/OL503464S
Christian A. Kuttruff, Martin D. Eastgate, Phil S. Baran, Natural product synthesis in the age of scalability. Natural Product Reports. ,vol. 31, pp. 419- 432 ,(2014) , 10.1039/C3NP70090A