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DOI: 10.1055/s-0040-1720032
Synthetic Approaches to Diospongins: A Two Decade Journey
The author Dr. Krishnaji acknowledges CHRIST (Deemed to be University) for funding though the Major Research Project (MRP # MRPDSC-1723).
Abstract
Tetrahydropyran units having multiple stereogenic centers serve as excellent building blocks for various active pharmaceutical ingredients (APIs). In particular, the presence of the unique molecular architecture of the trisubstituted tetrahydropyran (THP) unit in diospongins enhances their biological activity due to multiple stereogenic centers and has attracted attention from the synthetic community over the last two decades. In this review, we discuss synthetic approaches to chiral and racemic forms of diospongins during the period 2006–2020 in chronological order.
Key words
diospongins - diarylheptanoids - tetrahydropyran - cross-metathesis - hetero-Diels–Alder reaction - asymmetric allylation - enzyme resolution - oxa-Michael addition - Prins cyclizationPublication History
Received: 09 June 2022
Accepted after revision: 20 June 2022
Article published online:
14 July 2022
© 2022. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)
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References
- 1a Perron F, Albizati KM. Chem. Rev. 1989; 89: 1617
- 1b Shimizu YM. Chem. Rev. 1993; 93: 1685
- 1c Yasumoto T, Murata M. Chem. Rev. 1993; 93: 1897
- 1d lvarez AA. E, Candenas ML, Perez R, Ravelo JL, Martın JD. Chem. Rev. 1995; 95: 1953
- 2a Elliott MC. Contemp. Org. Synth. 1994; 1: 457
- 2b Burns CJ, Middleton DS. Contemp. Org. Synth. 1996; 3: 229
- 2c Elliott MC. Contemp. Org. Synth. 1997; 4: 238
- 2d Elliott MC. J. Chem. Soc., Perkin Trans. 1 1998; 4175
- 2e Elliott MC. J. Chem. Soc., Perkin Trans. 1 2000; 1291
- 2f Elliott MC, Williams E. J. Chem. Soc., Perkin Trans. 1 2001; 2303
- 2g Elliott MC. J. Chem. Soc., Perkin Trans. 1 2002; 2301
- 3a Clarke PA, Santos S. Eur. J. Org. Chem. 2006; 2045
- 3b Nasir NMd, Ermanis K, Clark PA. Org. Biomol. Chem. 2014; 12: 3323
- 3c Fuwa H. Mar. Drugs 2016; 14: 65
- 3d Tadiparthi K. ChemistrySelect 2021; 45: 12702
- 4 For a review on tetrahydrofuran-containing natural products, see: Fernandes RA, Pathare RS, Gorve DA. Chem. Asian J. 2020; 15: 2815
- 5a Zhu J, Islas-Gonzalez G, Bois-Choussy M. Org. Prep. Proced. Int. 2000; 32: 505
- 5b Claeson P, Claeson UP, Tuchinda P, Rentrakul V. Studies in Natural Product Chemistry, Vol. 26. Atta-ur-Rahman, Elsevier; Amsterdam: 2002: 881
- 5c Kadota S, Tezuka Y, Prasaim JK, Ali MS, Banskota AH. Curr. Top. Med. Chem. 2003; 3: 203
- 6a Scapagnini G, Colombrita C, Amadio M, D’Agata V, Arcelli E, Sapienza M, Quattrone A, Calabrese V. Antioxid. Redox Signaling 2006; 8: 395
- 6b Wang Z, Zhang Y, Banerjee S, Li Y, Sarkar FH. Cancer 2006; 106: 2503
- 7a Mohamad H, Lajis NH, Abas F, Ali AM, Sukari MA, Kibazuki H, Nakatani N. J. Nat. Prod. 2005; 68: 285
- 7b Kim J.-H, Lee KW, Lee M.-W, Lee HJ, Kim S.-H, Surh Y.-J. FEBS Lett. 2006; 580: 385
- 8 Yin J, Kouda K, Tezuka Y, Le Tran Q, Miyahara T, Chen Y, Kadota S. Planta Med. 2004; 70: 54
- 9a Tadiparthi K, Anand P, Sakirolla R, Gupta TP, Jadhav KA, Das SK, Yadav JS. Chem. Rec. 2022; 22: 60
- 9b Tadiparthi K, Roy A, Sakirolla R, Reddy BV. S, Yadav JS. Chem. Rec. 2022; e202200044
- 9c Tadiparthi K, Venkatesh S. J. Heterocycl. Chem. 2022; doi.org/10.1002/jhet.4480
- 9d Tadiparthi K, Anand P. Org. Process Res. Dev. 2021; 25: 2008
- 9e Tadiparthi K, Devaroy MJ. L, Panigrahi A, Sakirolla R. Asian J. Org. Chem. 2021; 8: 2084
- 9f Tadiparthi K, Anand P. Synthesis 2021; 53: 3469
- 10a Raghavendra S, Tadiparthi K, Yadav JS. Carbohydr. Res. 2017; 442: 17
- 10b Kamal A, Khanna GB. R, Krishnaji T. Helv. Chim. Acta 2007; 90: 1723
- 10c Tadiparthi K, Kamal A, Raghavendra S. Asian J. Chem. 2017; 29: 2321
- 10d Kamal A, Krishnaji T, Reddy PV. Tetrahedron: Asymmetry 2007; 18: 1775
- 10e Kamal A, Krishnaji T, Reddy PV. Tetrahedron Lett. 2007; 48: 7232
- 10f Kamal A, Krishnaji T, Khanna GB. R. Tetrahedron Lett. 2006; 47: 8657
- 11 Chandrasekhar S, Shyamsunder T, Prakash SJ, Prabhakar A, Jagadeesh B. Tetrahedron Lett. 2006; 47: 47 ; In this paper the product was named ‘(–)-diospongin B’; however, this isomer was subsequently referred to as ‘(–)-diospongin A’ in subsequent publications (compound 1 in this review)
- 12 Bressy C, Allais F, Cossy J. Synlett 2006; 3455
- 13 Sawant KB, Jennings M. J. Org. Chem. 2006; 71: 7911
- 14 Kawai N, Hande SM, Uenishi J. Tetrahedron 2007; 63: 9049
- 15 Wang H, Shuhler BT, Xian M. Synlett 2008; 2651
- 16 Yadav J, Padmavani B, Reddy BV. S, Venugopal Ch, Rao AB. Synlett 2007; 2045
- 17 Bates R, Song P. Tetrahedron Lett. 2007; 63: 4497
- 18 Sabitha G, Padmaja P, Yadav JS. Helv. Chim. Acta 2008; 91: 2235
- 19 Kumaraswamy G, Ramakrishna G, Naresh P, Jagadeesh B, Sridhar B. J. Org. Chem. 2009; 74: 8468
- 20 Anada M, Washio T, Watanabe Y, Takeda K, Hashimoto S. Eur. J. Org. Chem. 2010; 6850
- 21 Kumar RN, Meshram HM. Tetrahedron Lett. 2011; 52: 1003
- 22 Raffier L, Izquierdo F, Piva O. Synthesis 2011; 4037
- 23 Reddy ChR, Reddy GB, Srikanth B. Tetrahedron: Asymmetry 2011; 22: 1725
- 24 Shioiri T, McFarlane N, Hamada Y. Heterocycles 1998; 47: 73
- 25 Stefan E, Nalin AP, Taylor RE. Tetrahedron 2013; 69: 7706
- 26 Meruva SB, Mekala R, Raghunadh A, Rao KR, Dahanukar VH, Pratap TV, Kumar UK. S, Dubey PK. Tetrahedron Lett. 2014; 55: 4739
- 27 Zúñiga A, Pérez M, Gándara Z, Fall A, Gómez G, Fall Y. ARKIVOC 2015; (vii): 195
- 28 Rybak T, Hall DG. Org. Lett. 2015; 17: 4165
- 29 Clarke PA, Nasir NM, Sellars PB, Peter AM, Lawson CA, Burroughs JL. Org. Biomol. Chem. 2016; 14: 6840
- 30 Vaithegi K, Prasad KR. Tetrahedron 2020; 76: 131625
- 31 Hiebel M.-A, Pelotier B, Piva O. Tetrahedron 2007; 63: 7874
- 32 Lee K, Kim H, Hong J. Org. Lett. 2009; 11: 5202
- 33 More JD. Synthesis 2010; 2419
- 34 Karlubíkov O, Babjak M, Gracza T. Tetrahedron 2011; 67: 4980
- 35 Ho T.-L, Tang B, Ma G, Xu P. J. Chin. Chem. Soc. 2012; 59: 455
- 36 Yao H, Ren J, Tong R. Chem. Commun. 2013; 49: 193
- 37 Gharpure SJ, Mane SP, Nanda LN, Shukla MK. Isr. J. Chem. 2016; 56: 553
For reviews on oxygen-containing natural products, see:
For a series of review articles on the synthesis of saturated oxygen heterocycles, see:
For reviews on synthesis of tetrahydropyran derivatives, see:
Isolation and biological activity of diospongin: