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Synthesis 2015; 47(07): 1016-1023
DOI: 10.1055/s-0034-1380133
DOI: 10.1055/s-0034-1380133
paper
Total Synthesis of Laingolide A Diastereomers
Further Information
Publication History
Received: 03 December 2014
Accepted 08 January 2015
Publication Date:
11 February 2015 (online)
Abstract
The first total syntheses of two (±)-laingolide A diastereomers were achieved in 11 and 12 steps, respectively. The key steps include a tandem cross-dimerization/oxonia-Cope reaction and an intramolecular dehydrative cyclization for the formation of either the trans- or cis-enamide moieties.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380133.
- Supporting Information
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References
- 1 Klein D, Braekman J.-C, Daloze D, Hoffmann L, Demoulin V. Tetrahedron Lett. 1996; 37: 7519
- 2 Klein D, Braekman J.-C, Daloze D, Hoffmann L, Castillo G, Demoulin V. J. Nat. Prod. 1999; 62: 934
- 3 Matthew S, Salvador LA, Schupp PJ, Paul VJ, Luesch H. J. Nat. Prod. 2010; 73: 1544
- 4 Pereira AR, Cao Z, Engene N, Soria-Mercado IE, Murray TF, Gerwick WH. Org. Lett. 2010; 12: 4490
- 5a Tello-Aburto R, Johnson EM, Valdez CK, Maio WA. Org. Lett. 2012; 14: 2150
- 5b Tello-Aburto R, Newar TD, Maio WA. J. Org. Chem. 2012; 77: 6271
- 5c Wadsworth AD, Furkert DP, Sperry J, Brimble MA. Org. Lett. 2012; 14: 5374
- 5d Sudhakar G, Reddy KJ, Nanubolu JB. Tetrahedron 2013; 69: 2419
- 5e Philkhana SC, Seetharamsingh B, Dangat YB, Vanka K, Reddy DS. Chem. Commun. 2013; 49: 3342
- 5f Wadsworth AD, Furkert DP, Brimble MA. J. Org. Chem. 2014; 79: 11179
- 6 Mehrotra S, Duggan BM, Tello-Aburto R, Newar TD, Gerwick WH, Murray TF, Maio WA. J. Nat. Prod. 2014; 77: 2553
- 7a Echeverria P.-G, Prévost S, Cornil J, Férard C, Reymond S, Guérinot A, Cossy J, Ratovelomanana-Vidal V, Phansavath P. Org. Lett. 2014; 16: 2390
- 7b Prévost S, Ayad T, Phansavath P, Ratovelomanana-Vidal V. Adv. Synth. Catal. 2011; 353: 3213
- 7c Roche C, Desroy N, Haddad M, Phansavath P, Genet J.-P. Org. Lett. 2008; 10: 3911
- 8 Zou Y, Ding C, Zhou L, Li Z, Wang Q, Schoenebeck F, Goeke A. Angew. Chem. Int. Ed. 2012; 51: 5647
- 9a Huynh C, Derguini-Boumechal F, Linstrumelle G. Tetrahedron Lett. 1979; 20: 1503
- 9b Warrington JM, Barriault L. Org. Lett. 2005; 7: 4589
- 10 The relative configuration between the C(7) and C(9) stereocenters in compound 11 was assigned on the basis of NOESY experiments, and the trans relationship was later confirmed by an X-ray crystal structure analysis of the parent compound 15.
- 11 To ascertain that no enrichment in trans-11 at the expense of the cis-isomer occurred during the purification process, a sample of pure (Z)-10 was subjected to the hydrogenation reaction and the trans-isomer was obtained exclusively.
- 12 Formation of the cis-isomer can be rationalized by considering the most stable conformation of the 10-membered lactone enolate (boat–chair–boat conformation), see: Still WC, Galynker I. Tetrahedron 1981; 37: 3981
- 13 Epp JB, Widlanski TS. J. Org. Chem. 1999; 64: 293
- 14 Nakamura T, Noguchi T, Kobayashi H, Miyachi H, Hashimoto Y. Chem. Pharm. Bull. 2006; 54: 1709
- 15 Shea KJ, Wada E. J. Am. Chem. Soc. 1982; 104: 5715
- 16 Inanaga J, Hirata K, Saeki H, Katsuki T, Yamaguchi M. Bull. Chem. Soc. Jpn. 1979; 52: 1989