Synthesis, Inhaltsverzeichnis Synthesis 2021; 53(16): 2903-2910DOI: 10.1055/a-1500-1407 paper Unified Approach for the Total Synthesis of Bis-THF C15 Acetogenins: A Chloroenyne from Laurencia majuscula, Laurendecumenyne B and Laurefurenynes A/B Sibadatta Senapati a Division of Organic Chemistry, National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008, India b Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India , Nivedya A. Unmesh a Division of Organic Chemistry, National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008, India , Manoj N. Shet a Division of Organic Chemistry, National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008, India , Iram Ahmad a Division of Organic Chemistry, National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008, India , Nandu Ajikumar a Division of Organic Chemistry, National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008, India , Chepuri V. Ramana ∗ a Division of Organic Chemistry, National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008, India b Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India › Institutsangaben Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract A highly diastereoselective total synthesis of several bis-THF C15 acetogenin natural products, chloroenyne from Laurencia majuscula, laurendecumenyne B, and laurefurenynes A/B, is reported. Additionally the synthesis of an advanced intermediate reported in the earlier total synthesis of (E/Z)-elatenynes (formal synthesis) is described. The salient features in the synthesis include epoxide opening, Birch reduction, Sharpless asymmetric dihydroxylation-cycloetherification, SN2 halogenation, and a relay cross metathesis. Key words Key wordsbis-THF C15 acetogenins - carbohydrate building block - Sharpless asymmetric dihydroxylation-cycloetherification - SN2 halogenation - relay-cross-metathesis Volltext Referenzen References 1a Wanke T, Philippus AC, Zatelli GA, Vieira LF. O, Lhullier C, Falkenberg M. Rev. Bras. Farmacogn. 2015; 25: 569 1b Zhou ZF, Menna M, Cai Y.-S, Guo YW. Chem. Rev. 2015; 115: 1543 1c Neske A, Hidalgo JR, Cabedo N, Cortes D. Phytochemistry 2020; 174: 112332 1d Fernandes RA, Gorve DA, Pathare RS. Org. Biomol. Chem. 2020; 18: 7002 2a Hall JG, Reiss JA. Aust. J. Chem. 1986; 39: 1401 2b Ji N.-Y, Li X.-M, Li K, Wang B.-G. J. Nat. Prod. 2007; 70: 1499 2c Dias DA, Urban S. Phytochemistry 2011; 72: 2081 3 Wright AD, König GM, Nys RD, Sticher O. J. Nat. Prod. 1993; 56: 394 4 Abdel-Mageed WM, Ebel R, Valeriote FA, Jaspars M. Tetrahedron 2010; 66: 2855 5a Fukuzawa A, Aye M, Nakamura M, Tamura M, Murai A. Tetrahedron Lett. 1990; 31: 4895 5b Kikuchi H, Suzuki T, Kurosawa E, Suzuki M. Bull. Chem. Soc. Jpn. 1991; 64: 1763 6a Sheldrake HM, Jamieson C, Burton JW. Angew. Chem. Int. Ed. 2006; 45: 7199 6b Sheldrake HM, Jamieson C, Pascu SI, Burton JW. Org. Biomol. Chem. 2009; 7: 238 6c Dyson BS, Burton JW, Sohn T.-i, Kim B, Bae H. J. Am. Chem. Soc. 2012; 134: 11781 7 Shephard ED, Dyson BS, Hak WE, Nguyen QN. N, Lee M, Kim MJ, Sohn T.-i, Kim D, Burton JW, Paton RS. J. Org. Chem. 2019; 84: 4971 8 Shepherd DJ, Broadwith PA, Dyson BS, Paton RS, Burton JW. Chem. Eur. J. 2013; 19: 12644 9 Smith SG, Paton RS, Burton JW, Goodman JM. J. Org. Chem. 2008; 73: 4053 10 Holmes MT, Britton R. Chem. Eur. J. 2013; 19: 12649 11a Wang J, Tong R. Org. Chem. Front. 2017; 4: 140 11b Chhetri BK, Lavoie S, Sweeny-Jones AM, Kubanek J. Nat. Prod. Rep. 2018; 35: 514 12a Senapati S, Das S, Ramana CV. J. Org. Chem. 2018; 83: 12863 12b Chan HS. S, Nguyen QN. N, Paton RS, Burton JW. J. Am. Chem. Soc. 2019; 141: 15951 13a Mullapudi V, Ramana CV. Tetrahedron Lett. 2015; 56: 3933 13b Das S, Ramana CV. Tetrahedron 2015; 71: 8577 14 Mullapudi V, Ahmad I, Senapati S, Ramana CV. ACS Omega 2020; 5: 25334 15 Kona CN, Ramana CV. Tetrahedron 2014; 70: 3653 16 Marshall JA, Sabatini JJ. Org. Lett. 2005; 7: 4819 17a Kozikowski AP, Sorgi KL. Tetrahedron Lett. 1982; 23: 2281 17b Kozikowski AP, Sorgi KL, Wang BC, Xu ZB. Tetrahedron Lett. 1983; 24: 1563 17c Gaertzen O, Misske AM, Wolbers P, Hoffmann HM. R. Synlett 1999; 1041 17d Larsen CH, Ridgway BH, Shaw JT, Woerpel KA. J. Am. Chem. Soc. 1999; 121: 12208 17e García-Tellado F, de Armas P, Marrero-Tellado JJ. Angew. Chem. Int. Ed. 2000; 39: 2727 17f de Armas P, García-Tellado F, Marrero-Tellado JJ. Eur. J. Org. Chem. 2001; 2: 4423 17g Ghosh R, Maity JK, Achari B, Mandal SB. J. Org. Chem. 2010; 75: 2419 18 Shin I, Lee D, Kim H. Org. Lett. 2016; 18: 4420 19a Garber SB, Kingsbury JS, Gray BL, Hoveyda AH. J. Am. Chem. Soc. 2000; 122: 8168 19b Hansen EC, Lee D. Org. Lett. 2004; 6: 2035 19c Kim H, Lee H, Lee D, Kim S, Kim D. J. Am. Chem. Soc. 2007; 129: 2269 19d Cho EJ, Lee D. Org. Lett. 2008; 10: 257 19e Yun SY, Kim M, Lee D, Wink DJ. J. Am. Chem. Soc. 2009; 131: 24 19f Vougioukalakis GC, Grubbs RH. Chem. Rev. 2010; 110: 1746 Zusatzmaterial Zusatzmaterial Supporting Information Primärdaten Primary Data
