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Synlett 2017; 28(09): 1046-1050
DOI: 10.1055/s-0036-1588950
DOI: 10.1055/s-0036-1588950
letter
Toward the Stereoselective Synthesis of Arthrobotrisin A: Fragment Synthesis and Coupling Studies
Further Information
Publication History
Received: 20 November 2016
Accepted after revision: 20 January 2017
Publication Date:
24 February 2017 (online)
Abstract
A route towards the stereocontrolled synthesis of arthrobotrisin A based on a Nozaki–Hiyama–Kishi (NHK) coupling strategy was developed. Highlights of the fragment synthesis include enzyme-catalyzed kinetic resolution, Negishi carbometalation–iodination, quinone formation through oxidation with hypervalent iodine, chiral oxazaborolidine-catalyzed asymmetric Diels–Alder reaction with cyclopentadiene, regio- and stereoselective epoxidation, Noyori reduction, retro-Diels–Alder reaction, diastereoselective Luche reduction, and, finally, a Nozaki–Hiyama–Kishi (NHK) coupling of the vinyl iodide fragment.
Key words
arthrobotrisin A - Nozaki–Hiyama–Kishi coupling - Diels–Alder reaction - Noyori reduction - Luche reduction - asymmetric synthesisSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588950.
- Supporting Information
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References and Notes
- 1a Marco-Contelles J, Molina MT, Anjum S. Chem. Rev. 2004; 104: 2857-2857
- 1b Fraga BM. Nat. Prod. Rep. 2012; 29: 1334-1334
- 1c Raghavan S, Babu VS. Chem. Eur. J. 2011; 17: 8487-8487
- 2 Bugni TS, Ireland CM. Nat. Prod. Rep. 2004; 21: 143-143
- 3a Herath KB, Jayasuriya H, Bills GF, Polishook JD, Dombrowski AW, Guan Z, Felock P, Hazuda DJ. B, Singh SB. J. Nat. Prod. 2004; 67: 872-872
- 3b Mohamed IE, Gross H, Pontius A, Kehraus S, Krick A, Kelter G, Maier A, Fiebig H.-H, König GM. Org. Lett. 2009; 11: 5014-5014
- 4 Wei L.-X, Zhang H.-X, Tan J.-L, Chu Y.-S, Li N, Xue H.-X, Wang Y.-L, Niu X.-M, Zhang Y, Zhang K.-Q. J. Nat. Prod. 2011; 74: 1526-1526
- 5 Anderson MG, Jarman TB, Rickards RW. J. Antibiot. 1995; 48: 391-391
- 6a Kumar RN, Meshram HM. Tetrahedron Lett. 2011; 52: 1003-1003
- 6b Ramesh P, Meshram HM. Tetrahedron 2012; 68: 9289-9289
- 6c Kumar RN, Meshram HM. Tetrahedron 2015; 71: 5669-5669
- 6d Kumar NS, Kumar RN, Rao LC, Meshram HM. ChemistrySelect 2016; 1: 5034-5034
- 6e Kumar RN, Meshram HM. Pharma Chem. 2016; 8: 109-109
- 7a Li C, Lobkovsky E, Porco JA. Jr. J. Am. Chem. Soc. 2000; 122: 10484-10484
- 7b Shoji M, Yamaguchi J, Kakeya H, Osada H, Hayashi Y. Angew. Chem. Int. Ed. 2002; 41: 3192-3192
- 7c Mehta G, Pan SC. Org. Lett. 2004; 6: 3985-3985
- 7d Vannada J, Niehues L, König B, Mehta G. Tetrahedron 2013; 69: 6034-6034
- 7e Shoji M. Bull. Chem. Soc. Jpn. 2007; 80: 1672-1672
- 7f Shoji M, Hayashi Y. Eur. J. Org. Chem. 2007; 2007: 3783-3783
- 8 Tamura Y, Yakura T, Tohma H, Ki-kuchi K, Kita Y. Synthesis 1989; 126-126
- 9a Nicolaou KC, Li H, Nold AL, Pappo D, Lenzen A. J. Am. Chem. Soc. 2007; 129: 10356-10356
- 9b Peyton III J, Callery PS, Shulgin AT, Castagnoli NJr. J. Org. Chem. 1976; 41: 3627-3627
- 9c Yakura T, Konishi T. Synlett 2007; 765-765
- 9d Yakura T, Tian Y, Yamauchi Y, Omoto M, Konishi T. Chem. Pharm. Bull. 2009; 57: 252-252
- 9e Yakura T, Ozono A, Morimoto K. Chem. Pharm. Bull. 2011; 59: 132-132
- 10a Ryu DH, Lee TW, Corey EJ. J. Am. Chem. Soc. 2002; 124: 9992-9992
- 10b Corey EJ, Shibata T, Lee TW. J. Am. Chem. Soc. 2002; 124: 3808-3808
- 10c Ichihara A, Kobayashi M, Oda K, Sakamura S. Bull. Chem. Soc. Jpn. 1978; 51: 826-826
- 10d Herzon SB, Calandra NA, King SM. Angew. Chem. Int. Ed. 2011; 50: 8863-8863
- 10e Klunder AJ. H, Zwanenburg JZ. Chem. Rev. 1999; 99: 1163-1163
- 11 The enantioselectivity was determined by HPLC analysis using a CHIRALPAK OD-H 250 × 4.6 mm, 5 μm column (2% i-PrOH–hexanes; 1 mL/min; λ = 254 nm); T R = 9.93 min (minor), 11.1 min (major).
- 12a Yadav VK, Kapoor KK. Tetrahedron 1995; 51: 8573-8573
- 12b Genski T, Macdonald G, Wei X, Lewis N, Taylor RJ. K. Synlett 1999; 795-795
- 13a Mehta G, Pan SC. Tetrahedron Lett. 2005; 46: 3045-3045
- 13b Mehta G, Roy S. Tetrahedron Lett. 2008; 49: 1458-1458
- 14 Clay DR, Rosenberg AG, McIntosh MC. Tetrahedron: Asymmetry 2011; 22: 713-713
- 15 The diastereoselectivity was determined by HPLC analysis using an XSELECTC18, 4.6 × 150 mm, 5 μm column (60% MeCN–H2O + 0.1% FA; 1 mL/min; λ = 210 nm); t R = 4.4 min (minor), 4.7 min (major).
- 16 Gemal AL, Luche JL. J. Am. Chem. Soc. 1981; 103: 5454-5454
- 17a Peterson MA, Polt R. J. Org. Chem. 1993; 58: 4309-4309
- 17b Hamada M, Higashi T, Shoji M, Umezawa K, Sugai T. J. Mol. Catal. B: Enzym. 2010; 67: 78-78
- 18a Rhode O, Hoffmann HM. R. Tetrahedron 2000; 56: 6479-6479
- 18b Justicia J, Sancho-Sanz I, Álvarez-Manzaneda E, Oltra JE, Cuerva JM. Adv. Synth. Catal. 2009; 351: 2295-2295
- 18c Shirley HJ, Bray CD. Eur. J. Org. Chem. 2016; 1504-1504
- 18d Calleja P, Michael ME, Jiménez T, Echavarren AM. Synthesis 2016; 48: 3183-3183
- 19 Rachwalski M, Vermue N, Rutjes FP. J. T. Chem. Soc. Rev. 2013; 42: 9268-9268
- 20a Seco JM, Quiñoá E, Riguera R. Chem. Rev. 2004; 104: 17-17
- 20b Dale JA, Mosher HS. J. Am. Chem. Soc. 1973; 95: 512-512 (For mandelate ester analysis data, see the Supporting Information)
- 21 Negishi E, Van Horn DE, Yoshida T. J. Am. Chem. Soc. 1985; 107: 6639-6639
- 22 Kress MH, Ruel R, Miller WH, Kishi Y. Tetrahedron 1993; 34: 6003-6003