Stereoselective Total Synthesis of Macrolide Sch-725674 and C-7-epi-Sch-725674

Karunakar Baikadi; Anil Talakokkula; A. Venkat Narsaiah

doi:10.1055/s-0037-1611665

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CC BY-ND-NC 4.0 · SynOpen 2019; 03(01): 26-35
DOI: 10.1055/s-0037-1611665

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Stereoselective Total Synthesis of Macrolide Sch-725674 and C-7-epi-Sch-725674

Karunakar Baikadi

,

Anil Talakokkula

,

A. Venkat Narsaiah*

Organic Synthesis Laboratory, Fluoro-Agrochemicals Department, CSIR-Indian Institute of Chemical Technology, Hyderabad, 500007, Telangana, India Email: vnakkirala2001@yahoo.com Email: vnakkirala@csiriict.in

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Abstract

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Abstract

The stereoselective total synthesis of Sch-725674 in 14 linear synthetic steps with 10.3% overall yield is described. The synthesis started from commercially available starting materials, d-ribose and (R)-benzyl glycidol. The key reactions involved CBS reduction, Julia–Kocienski olefination, Horner–Wadsworth–Emmons reaction, and Shiina macrolactonization.

Keywords

natural product synthesis - macrolides - Sch-725674 - C-7-epi-Sch-725674 - antifungal agents

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References

References
1 Yang SW, Chan TM, Terracciano J, Loebenberg D, Patel M, Chu M. J. Antibiot. 2005; 58: 535
2 Moretti JD, Wang X, Curran DP. J. Am. Chem. Soc. 2012; 134: 7963

3a Bali AK, Sunnam SK, Prasad KR. Org. Lett. 2014; 16: 4001
3b Sunnam SK, Prasad KR. Tetrahedron 2014; 70: 2096
3c Ramakrishna K, Kaliappan KP. Org. Biomol. Chem. 2015; 13: 234
3d Seetharamsingh B, Khairnar PV, Reddy DS. J. Org. Chem. 2016; 81: 290
3e Sharma BM, Gontala A, Kumar P. Eur. J. Org. Chem. 2016; 1215
3f Bodugam M, Javed S, Ganguly A, Torres J, Hanson PR. Org. Lett. 2016; 18: 516
3g Reddy Y, Sabitha G. ChemistrySelect 2016; 1: 2156

4a Nagalatha G, Narala SG, Narsaiah AV. SynOpen 2018; 2: 251
4b Ghogare RS, Wadavrao SB, Narsaiah AV. Helv. Chim. Acta 2016; 99: 247
4c Wadavrao SB, Ghogare RS, Narsaiah AV. Helv. Chim. Acta 2015; 98: 575
4d Wadavrao SB, Ghogare RS, Narsaiah AV. Synthesis 2015; 2129
4e Narala SG, Nagalatha G, Narsaiah AV. ARKIVOC 2018; (vii): 495

5a Bonini C, Chiummiento L, Pullez M, Solladié G, Colobert F. J. Org. Chem. 2004; 69: 5015
5b Huang H, Mao C, Jan S.-T, Uckun FM. Tetrahedron Lett. 2000; 41: 1699

6a Dachavaram SS, Kalyankar KB, Das S. Tetrahedron Lett. 2014; 55: 5629
6b Yadav JS, Lakshmi PN, Harshavardhan SJ, Reddy BV. S. Synlett 2007; 1945
6c Wadavrao SB, Ghogare RS, Narsaiah AV. Tetrahedron Lett. 2012; 53: 3955
6d Narsaiah AV, Ghogare RS. Synthesis 2011; 3271
6e Wadavrao SB, Ghogare RS, Narsaiah AV. Synthesis 2015; 47: 2129

7a Evans DA, Dow RL, Shih TL, Takacs JM, Zahler R. J. Am. Chem. Soc. 1990; 112: 5290
7b Lowe JT, Wrona IE, Panek JS. Org. Lett. 2007; 9: 327

8a Clyne DS, Weiler L. Tetrahedron 1999; 55: 13659
8b Yadav JS, Thirupathaiah B, Singh VK, Ravishashidhar V. Tetrahedron: Asymmetry 2012; 23: 931
8c Nakayama Y, Maeda Y, Hama N, Sato T, Chida N. Synthesis 2016; 1647

9 Das S, Kuilya TK, Goswami RK. J. Org. Chem. 2015; 80: 6467

10a Yahata K, Ye N, Iso K, Ai Y, Lee J, Kishi Y. J. Org. Chem. 2017; 82: 8808
10b Kesenheimer C, Groth U. Org. Lett. 2006; 8: 2507
10c Ganganna B, Srihari P, Yadav JS. Tetrahedron Lett. 2017; 58: 2685

11 Davies SG, Foster EM, Lee JA, Roberts PM, Thomson JE. Tetrahedron: Asymmetry 2014; 25: 534

12a Rao MV, Naresh A, Saketh G, Rao BV. Tetrahedron Lett. 2013; 54: 6931
12b Ghogare RS, Wadavrao SB, Narsaiah AV. Tetrahedron Lett. 2013; 54: 5674

13 Abe K, Kato K, Arai T, Rahim MA, Sultana I, Matsumura S, Toshima K. Tetrahedron Lett. 2004; 45: 8849
14 Trost BM, O’Boyle BM. J. Am. Chem. Soc. 2008; 130: 16190
15 Kirkham JE. D, Courtney TD. L, Lee V, Baldwin JE. Tetrahedron 2005; 61: 7219
16 Hung DT, Nerenberg JB, Schreiber SL. J. Am. Chem. Soc. 1996; 118: 11054

17a Tap A, Jouanneau M, Galvani G, Sorin G, Lannou M.-I, Férézoub J.-P, Ardisson J. Org. Biomol. Chem. 2012; 10: 8140
17b Sabitha G, Reddy CN, Raju A, Yadav JS. Tetrahedron: Asymmetry 2011; 22: 493

18 Manikanta G, Nagaraju T, Krishna PR. Synthesis 2016; 48: 4213
19 Butler SC, Forsyth CJ. J. Org. Chem. 2013; 78: 3895
20 Lebar MD, Baker BJ. Tetrahedron 2010; 66: 1557
21 Si D, Sekara NM, Kaliappan KP. Org. Biomol. Chem. 2011; 9: 6988

22a Njardarson JT, Gaul C, Shan D, Huang X.-Y, Danishefsky SJ. J. Am. Chem. Soc. 2004; 126: 1038
22b Reymond S, Cossy J. Tetrahedron 2007; 63: 5918

23a Jena BK, Reddy GS, Mohapatra DK. Org. Biomol. Chem. 2017; 15: 1863
23b Kim H, Hong J. Org. Lett. 2010; 12: 2880

24 Pandey SK, Kumar P. Tetrahedron Lett. 2005; 46: 6625

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