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Synthesis 2014; 46(09): 1177-1184
DOI: 10.1055/s-0033-1340853
DOI: 10.1055/s-0033-1340853
paper
Total Synthesis of the Z-Isomers of the Proposed and Revised Structures of Aspergillide B via an Iodocyclization and Ring-Closing Metathesis Strategy
Further Information
Publication History
Received: 04 January 2014
Accepted after revision: 03 February 2014
Publication Date:
26 February 2014 (online)
Abstract
The synthesis of Z-isomers of both the proposed and revised structures of aspergillide B is described. A divergent route is employed that involves kinetically controlled ring-closing metathesis for the construction of a 14-membered macrocyclic ring, ester formation under Yamaguchi conditions, a Wacker-type oxidative cyclization for creation of the C4 stereogenic center and a previously reported diastereoselective isomerization–iodocyclization strategy for the construction of the 2,6-trans-disubstituted tetrahydropyran subunit.
Key words
aspergillides - ring-closing metathesis - Yamaguchi esterification - Wacker-type oxidation - iodocyclization - cytotoxic activitySupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1 Kito K, Ookura R, Yoshida S, Namikoshi M, Ooi T, Kusumi T. Org. Lett. 2008; 10: 225
- 2 Hande SM, Uenishi J. Tetrahedron Lett. 2009; 50: 189
- 3a Ookura R, Kito K, Saito Y, Kusumi T, Ooi T. Chem. Lett. 2009; 38: 384
- 3b Kito K, Ookura R, Yoshida S, Namikoshi M, Ooi T, Kusumi T. Org. Lett. 2008; 10: 225
- 4a Nagasawa T, Kuwahara S. Tetrahedron Lett. 2010; 51: 875
- 4b Diaz-Oltra S, Angulo-Pachon CA, Murga J, Carda M, Marco JA. J. Org. Chem. 2010; 75: 1775
- 4c Fuwa H, Yamaguchi H, Sasaki M. Org. Lett. 2010; 12: 1848
- 4d Fuwa H, Yamaguchi H, Sasaki M. Tetrahedron 2010; 66: 7492
- 4e Sabitha G, Reddy DV, Rao AS, Yadav JS. Tetrahedron Lett. 2010; 51: 4195
- 4f Díaz-Oltra S, Angulo-Pachón CA, Murga J, Falomir E, Carda M, Marco JA. Chem. Eur. J. 2011; 17: 675
- 4g Kanematsu M, Yoshida M, Shishido K. Angew. Chem. Int. Ed. 2011; 50: 2618 ; Angew. Chem. 2011, 123, 2666
- 4h Nagasawa T, Nukada T, Kuwahara S. Tetrahedron 2011; 67: 2882
- 4i Izuchi Y, Kanomata N, Koshino H, Hongo Y, Nakata T, Takahashi S. Tetrahedron: Asymmetry 2011; 22: 246
- 4j Zúñiga A, Pérez M, González M, Gómez G, Fall Y. Synthesis 2011; 3301
- 4k Sharma GV. M, Manohar V. Tetrahedron: Asymmetry 2012; 23: 252
- 5a Hande SM, Uenishi J. Tetrahedron Lett. 2009; 50: 189
- 5b Diaz-Oltra S, Angulo-Pachon CA, Kneeteman C, Murga J, Carda M, Marco JA. Tetrahedron Lett. 2009; 50: 3783
- 5c Nagasawa T, Kuwahara S. Biosci. Biotechnol. Biochem. 2009; 73: 1893
- 5d Liu J, Xu K, He J, Zhang L, Pan X, She X. J. Org. Chem. 2009; 74: 5063
- 5e Mueller AJ, Jennings MP. Tetrahedron Lett. 2010; 51: 4260
- 5f Trost BM, Bartlett MJ. Org. Lett. 2012; 14: 1322
- 5g Sridhar Y, Srihari P. Eur. J. Org. Chem. 2013; 578
- 6a Nagasawa T, Kuwahara S. Org. Lett. 2009; 11: 761
- 6b Panarese JD, Waters SP. Org. Lett. 2009; 11: 5086
- 6c Kanematsu M, Yoshida M, Shishido K. Tetrahedron Lett. 2011; 52: 1372
- 6d Kobayashi H, Kanematsu M, Yoshida M, Shishido K. Chem. Commun. 2011; 47: 7440
- 6e Srihari P, Sridhar Y. Eur. J. Org. Chem. 2011; 6690
- 7a Mohapatra DK, Das PP, Pattanayak MR, Yadav JS. Chem. Eur. J. 2010; 16: 2072
- 7b Mohapatra DK, Bhimireddy E, Krishnarao PS, Das PP, Yadav JS. Org. Lett. 2011; 13: 744
- 7c Yadav JS, Pattanayak MR, Das PP, Mohapatra DK. Org. Lett. 2011; 13: 1710
- 7d Mohapatra DK, Maity S, Rao TS, Yadav JS, Sridhar B. Eur. J. Org. Chem. 2013; 2859
- 8a Jena B, Mohapatra DK. Tetrahedron Lett. 2013; 54: 3415
- 8b Pradhan TR, Mohapatra DK. Tetrahedron: Asymmetry 2012; 23: 709
- 8c Mohapatra DK, Pattanayak MR, Das PP, Pradhan TR, Yadav JS. Org. Biomol. Chem. 2011; 9: 5630
- 8d Thirupathi B, Gundapaneni RR, Mohapatra DK. Synlett 2011; 2667
- 8e Mohapatra DK, Reddy DP, Dash U, Yadav JS. Tetrahedron Lett. 2011; 52: 151
- 8f Mohapatra DK, Somaiah R, Rao MM, Caijo F, Mauduit M, Yadav JS. Synlett 2010; 1223
- 8g Mohapatra DK, Dash U, Naidu PR, Yadav JS. Synlett 2009; 2129
- 8h Mohapatra DK, Sahoo G, Ramesh DK, Sastry GN. Tetrahedron Lett. 2009; 50: 5636
- 8i Mohapatra DK, Rahman H, Pal R, Gurjar MK. Synlett 2008; 1801
- 8j Mohapatra DK, Ramesh DK, Giardello MA, Chorghade MS, Gurjar MK, Grubbs RH. Tetrahedron Lett. 2007; 48: 2621
- 8k Gurjar MK, Karmakar S, Mohapatra DK. Tetrahedron Lett. 2004; 45: 4525
- 9 Inanaga J, Hirata K, Saeki H, Katsuki T, Yamaguchi M. Bull. Chem. Soc. Jpn. 1979; 52: 1989
- 10 Kim MY, Kim H, Tae J. Synlett 2009; 1303
- 11 Yu W, Mei Y, Hua Z, Jin Z. Org. Lett. 2004; 6: 3217
- 12 Bal BS, Childers WE, Pinnick HW. Tetrahedron 1981; 37: 2091
-
13 Larock RC, Hightower TR. J. Org. Chem. 1993; 58: 5298
- 14 Sibi MP. Org. Prep. Proced. Int. 1993; 25: 15
- 15 Schultz AG, Kirincich SJ. J. Org. Chem. 1996; 61: 5626
-
16a Neises B, Steglich W. Angew. Chem. Int. Ed. 1978; 17: 522
- 16b Williams A, Ibrahim TI. Chem. Rev. 1981; 81: 589
- 16c Mikolajczyk M, Kielbasiński P. Tetrahedron 1981; 37: 233
- 17 More JD, Finney NS. Org. Lett. 2002; 4: 3001
For syntheses of aspergillide A, see:
For syntheses of aspergillide B, see:
For syntheses of aspergillide C, see:
For recent applications of iodocyclizations, see:
For our recent contributions to natural product synthesis using ring-closing metathesis reactions, see: