Stereoselective Synthesis of the C19–C39 Fragment of Bastimolide A

Nemilikonda Sravan Kumar; B. Janaki Ramulu; Subhash Ghosh

doi:10.1055/a-1647-7202

SynOpen, Inhaltsverzeichnis

CC BY-NC-ND 4.0 · SynOpen 2021; 05(04): 285-290
DOI: 10.1055/a-1647-7202

paper

Stereoselective Synthesis of the C19–C39 Fragment of Bastimolide A

Nemilikonda Sravan Kumar

^aDepartment of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad-500007, India

^bAcademy of Scientific and Innovative Research (AcSIR), Ghaziabad 201 002, India

,

B. Janaki Ramulu

^aDepartment of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad-500007, India

,

Subhash Ghosh ∗

^aDepartment of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad-500007, India

^bAcademy of Scientific and Innovative Research (AcSIR), Ghaziabad 201 002, India

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

This paper describes the synthesis of the C19–C39 fragment of the antimalarial natural product bastimolide A via addition of a functionalized C19–C26 alkyne fragment to a C27–C39 aldehyde fragment. Opening of a terminal epoxide and Noyori asymmetric reduction were used as key steps in the synthesis.

Key words

bastimolide A - antimalarial activity - stereoselective synthesis - epoxide opening - Noyori asymmetric reduction

Volltext

Referenzen

References

1a Pallela R, Na-Young Y, Kim SK. Mar. Drugs 2010; 8: 1189
1b Kuttruff CA, Eastgate MD, Baron PS. Nat. Prod. Rep. 2014; 31: 419
1c Blunt JW, Copp BR, Keyzers RA, Munro MH. G, Prinsep MR. Nat. Prod. Rep. 2012; 29: 144

2 Shao C.-L, Linington RG, Balunas MJ, Centeno A, Boudreau P, Zhang C, Engene N, Spadafora C, Mutka TS, Kyle DE, Gerwick L, Wang C.-Y, Gerwick WH. J. Org. Chem. 2015; 80: 7849

3a Ghosh S, Kumar SU, Shashidhar J. J. Org. Chem. 2008; 73: 1582
3b Ghosh S, Pradhan TK. J. Org. Chem. 2010; 75: 2107
3c Athe S, Chandrasekhar B, Roy S, Pradhan TK, Ghosh S. J. Org. Chem. 2012; 77: 9840
3d Reddy KM, Yamini V, Singarapu KK, Ghosh S. Org. Lett. 2014; 16: 2658
3e Chandrasekhar B, Athe S, Reddy PP, Ghosh S. Org. Biomol. Chem. 2015; 13: 115
3f Rao KN, Kanakaraju M, Kunwar AC, Ghosh S. Org. Lett. 2016; 18: 4092
3g Athe A, Sharma A, Marumudi K, Ghosh S. Org. Biomol. Chem. 2016; 14: 6769
3h Sharma A, Athe S, Ghosh S. ACS Omega 2018; 3: 16563

4 Quintard A, Sperandio C, Rodriguez J. Org. Lett. 2018; 20: 5274
5 Schleicher DK, Jamison TF. Beilstein J. Org. Chem. 2013; 9: 1533

6a Chang J, Paquette LA. Org. Lett. 2002; 4: 253
6b Paquette LA, Chang J, Liu Z. J. Org. Chem. 2004; 69: 6441

7 Sayini R, Srihari P. Synthesis 2018; 50: 663
8 Nicolaou KC, Daines RA, Uenishi J, Li WS, Papahatjis PD, Chakraborty TK. J. Am. Chem. Soc. 1988; 110: 4672
9 Bujaranipalli S, Das S. Tetrahedron: Asymmetry 2016; 27: 254
10 Cook C, Guinchard X, Liron F, Roulland E. Org. Lett. 2010; 12: 744
11 Nilewski C, Deprez NR, Fessard TC, Li D, Geisser RW, Carreira EM. Angew. Chem. Int. Ed. 2011; 50: 7940
12 Dess DB, Martin JC. J. Am. Chem. Soc. 1991; 113: 7277
13 Matsumura K, Hashiguchi S, Ikariya T, Noyori R. J. Am. Chem. Soc. 1997; 119: 8738

Zusatzmaterial

Supporting Information