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DOI: 10.1055/a-1500-1407
Unified Approach for the Total Synthesis of Bis-THF C15 Acetogenins: A Chloroenyne from Laurencia majuscula, Laurendecumenyne B and Laurefurenynes A/B
Authors acknowledge CSIR for generous research funding and for a research fellowship to SS.
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
bis-THF C15 acetogenins - carbohydrate building block - Sharpless asymmetric dihydroxylation-cycloetherification - SN2 halogenation - relay-cross-metathesisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1500-1407. Included are 13C chemical shifts comparison tables and NMR spectra of all new compounds.
- Supporting Information
Primary Data
- Primary Data
Primary data for this article are available online at https://doi.org/10.5281/zenodo.4733377. NMR FID files of all new compounds are available.
Publication History
Received: 09 April 2021
Accepted after revision: 05 May 2021
Accepted Manuscript online:
05 May 2021
Article published online:
02 June 2021
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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