RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00032269.xml
CC BY 4.0 · SynOpen 2022; 06(04): 312-318
DOI: 10.1055/s-0042-1751381
DOI: 10.1055/s-0042-1751381
paper
Stereoselective Synthesis of Euscapholide and Tetraketide via Prins Cyclisation and Ring-Closing Metathesis
Financial support was provided by the Council of Scientific and Industrial Research (CSIR), New Delhi.
Abstract
A concise and diastereoselective total synthesis of tetraketide and euscapholide is described in ten steps in 10.6% overall yield from acetaldehyde and (S)-pent-4-ene-1,2-diol. Jacobsen hydrolytic kinetic resolution, Prins cyclization, ring-closing metathesis and oxa-Michael addition reactions are the key steps involved in the synthesis.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751381.
- Supporting Information
Publikationsverlauf
Eingereicht: 12. September 2022
Angenommen nach Revision: 13. Oktober 2022
Artikel online veröffentlicht:
24. November 2022
© 2022. This is an open access article published by Thieme under the terms of the Creative Commons Attribution 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/4.0/)
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1 Cragg GM, Newman DJ. Pure Appl. Chem. 2005; 77: 7
- 2 Yoshio T, Yoshihiro O, Toshiya M, Eiji HA. T, Hideaki O. Phytochemistry 1998; 49: 2565
- 3a Drewes SE, Sehlapelo BM, Horn MM, Scott-Shaw R, Sandor P. Phytochemistry 1995; 38: 1427
- 3b Drewes SE, Horn MM, Shaw RS. Phytochemistry 1995; 40: 321
- 3c Jiang Z.-H, Yang Q.-X, Tanaka T, Kouno I. J. Nat. Prod. 2008; 71: 724
- 4a Fang X, Anderson JE, Chang C, Fanwick PE, McLaughlin JL. J. J. Chem. Soc., Perkin Trans. 1 1990; 1655
- 4b Fang XP, Anderson JE, Chang CJ, McLaughlin JL, Fanwick PE. J. Nat. Prod. 1991; 54: 1034
- 4c Goh SH, Ee GC. L, Chuah CH, Wei C. Aust. J. Chem. 1995; 48: 199
- 4d Mu Q, Tang W, Li C, Lu Y, Sun H, Zheng X, Wu N, Lou L, Xu B. Heterocycles 1999; 51: 2969
- 4e Takeda Y, Okada Y, Masuda T, Hirata E, Shinzato T, Takushi A, Yu Q, Otsuka H. Chem. Pharm. Bull. 2000; 48: 752
- 4f Lan YH, Chang FR, Yu JH, Yang YL, Chang YL, Lee SJ, Wu YC. J. Nat. Prod. 2003; 66: 487
- 4g Jiang ZH, Yang QX, Tanaka T, Kouno IJ. J. Nat. Prod. 2008; 71: 724
- 4h Sohn JH, Oh H. Bull. Korean Chem. Soc. 2010; 31: 1695
- 4i Liou JR, Wu TY, Thang TD, Hwang TL, Wu CC, Cheng YB, Chiang MY, Lan YU, Shazly ME, Wu SL, Beerhues L, Yuan SS, Hou MF, Chen SL, Chang FR, Wu YC. J. Nat. Prod. 2014; 77: 2626
- 4j Liu Y, Rakotondraibe LH, Brodie PJ, Wiley JD, Cassera MB, Miller JS, Ratovoson F, Rakotobe E, Rasamison VE, Kingston DG. I. J. Nat. Prod. 2015; 78: 1330
- 4k Dong M, Zhang Q, Hirota M. Tian. Chan. Yau. Yu. Kaifa 2004; 16: 290 ; Chem. Abstr. 2004, 143, 33891
- 4l Hsu FL, Chen YC, Cheng JT. Planta Med. 2000; 66: 228
- 5a Lee HY, Sampath V, Yoon Y. Synlett 2009; 249
- 5b Sabitha G, Srinivas C, Sudkakar K, Rajkumar M, Maruthi C, Yadav JS. Synthesis 2007; 3886
- 5c Albury AM. M, Jennings MP. J. Org. Chem. 2012; 77: 6929
- 5d Mohapatra DK, Krishnarao PS, Bhimireddy E, Yadav JS. Synthesis 2014; 1639
- 5e Prasad KR, Gholap SL. J. Org. Chem. 2008; 73: 2
- 5f Sabitha G, Reddy TR, Yadav JS. Tetrahedron Lett. 2011; 52: 6550
- 5g Kumaraswamy G, Kumar RS. Helv. Chim. Acta 2013; 96: 1366
- 6a Gupta P, Naidu SV, Kumar P. Tetrahedron Lett. 2005; 46: 6571
- 6b Yadav JS, Kumar NN, Sridhar Reddy M, Prasad AR. Tetrahedron 2007; 63: 2689
- 6c Garaas SD, Hunter TJ, O’Doherty GA. J. Org. Chem. 2002; 67: 2682
- 6d George S, Sudalai A. Tetrahedron: Asymmetry 2007; 18: 975
- 7 Padhi B, Sudhakar Reddy G, Mohapatra DK. J. Nat. Prod. 2016; 79: 2788
- 8a Yadav JS, Narasimhulu G, Mallikarjuna Reddy N, Subba Reddy BV. Tetrahedron Lett. 2010; 51: 1574
- 8b Yadav JS, Thrimurtulu N, Rahman MA, Satyanarayana Reddy J, Prasad AR, Subba Reddy BV. Synthesis 2010; 3657
- 9a Furrow ME, Schaus SE, Jacobsen EN. J. Org. Chem. 1998; 63: 6776
- 9b Nielsen LP. C, Zuend SJ, Ford DD, Jacobsen EN. J. Org. Chem. 2012; 77: 2486
- 10 Boninia C, Chiummiento L, Lopardo MT, Pullez M, Colobert F, Solladié G. Tetrahedron Lett. 2003; 44: 2695
- 11a Yadav JS, Reddy MS, Prasad AR. Tetrahedron Lett. 2005; 46: 2133
- 11b Ramachandran PV, Subash JC, Bodhuri P, Debarshi P, Venkat MR. R. Org. Biomol. Chem. 2005; 3: 3812
- 12a Barry CSt. J, Crosby SR, Harding JR, Hughes RA, King CD, Parker GD, Willis CL. Org. Lett. 2003; 5: 2429
- 12b Yang X.-F, Mague JT, Li C.-J. J. Org. Chem. 2001; 66: 739
- 12c Aubele DL, Wan S, Floreancig PE. Angew. Chem. Int. Ed. 2005; 44: 3485
- 12d Barry CS, Bushby N, Harding JR, Willis CS. Org. Lett. 2005; 7: 2683
- 12e Cossey KN, Funk RL. J. Am. Chem. Soc. 2004; 126: 12216
- 12f Crosby SR, Harding JR, King CD, Parker GD, Willis CL. Org. Lett. 2002; 4: 3407
- 12g Marumoto S, Jaber JJ, Vitale JP, Rychnovsky SD. Org. Lett. 2002; 4: 3919
- 12h Kozmin SA. Org. Lett. 2001; 3: 755
- 12i Jaber JJ, Mitsui K, Rychnovsky SD. J. Org. Chem. 2001; 66: 4679
- 12j Kopecky DJ, Rychnovsky SD. J. Am. Chem. Soc. 2001; 123: 8420
- 12k Rychnovsky SD, Thomas CR. Org. Lett. 2000; 2: 1217
- 12l Rychnovsky SD, Yang G, Hu Y, Khire UR. J. Org. Chem. 1997; 62: 3022
- 12m Su Q, Panek JS. J. Am. Chem. Soc. 2004; 126: 2425
- 12n Yadav JS, Reddy BV. S, Sekhar KC, Gunasekar D. Synthesis 2001; 885
- 12o Yadav JS, Reddy BV. S, Reddy MS, Niranjan N. J. Mol. Catal. A: Chem. 2004; 210: 99
- 12p Yadav JS, Reddy BV. S, Reddy MS, Niranjan N, Prasad AR. Eur. J. Org. Chem. 2003; 1779
- 13a Yadav JS, Reddy MS, Rao PP, Prasad AR. Tetrahedron Lett. 2006; 47: 4397
- 13b Yadav JS, Reddy MS, Prasad AR. Tetrahedron Lett. 2006; 47: 4937
- 13c Yadav JS, Reddy MS, Prasad AR. Tetrahedron Lett. 2005; 46: 2133
- 13d Yadav JS, Reddy MS, Prasad AR. Tetrahedron Lett. 2006; 47: 4995
- 13e Yadav JS, Reddy MS, Rao PP, Prasad AR. Synlett 2007; 2049
- 13f Yadav JS, Rao PP, Reddy MS, Rao NV, Prasad AR. Tetrahedron Lett. 2007; 48: 1469
- 13g Yadav JS, Kumar NN, Reddy MS, Prasad AR. Tetrahedron 2007; 63: 2689
- 13h Rao AV. R, Reddy ER, Joshi BV, Yadav JS. Tetrahedron Lett. 1987; 28: 6497
- 14 Kong X, Grindley TB. Can. J. Chem. 1994; 72: 2396
- 15 Sabitha G, Rao AS, Yadav JS. Org. Biomol. Chem. 2013; 11: 7218
- 16 Brun E, Bellosta V, Cossy J. J. Org. Chem. 2015; 80: 8668
- 17a Yadav JS, Reddy MS, Rao PP, Prasad AR. Tetrahedron Lett. 2006; 47: 4397
- 17b Brun E, Bellosta V, Cossy J. Chem. Commun. 2014; 50: 6718
- 18a Choon HT, Yoshihisa K, Yoshitokishi K. Angew. Chem. Int. Ed. 2000; 4282
- 18b Pereira CL, Chen Y.-H, McDonald FE. J. Am. Chem. Soc. 2009; 131: 6066
- 18c Wu B, Mallinger A. Org. Lett. 2010; 12: 2818
- 19 Chakraborty TK, RamkrishnaV R, Chattopadhyay AK. Tetrahedron Lett. 2006; 42: 7435
- 20a Mitsunobu O. Synthesis 1981; 1: 1
- 20b Dembinski R. Eur. J. Org. Chem. 2004; 2763
- 20c Ahn C, Correia R, Deshong P. J. Org. Chem. 2002; 67: 175
- 20d Mitsunobu O, Yamada M. Bull. Chem. Soc. Jpn. 1967; 40: 2380
- 21 Grubbs RH. Handbook of Metathesis . Wiley; New York: 2003. 2, 296
- 22 Subhash G, Rao NN. Tetrahedron Lett. 2010; 51: 2052
- 23 Yoshio T, Yoshihiro O, Toshiya M, Eiji HA. T, Hideaki O. Phytochemistry 1998; 49: 2565
For the Prins cyclization, see, for example: