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-00000084.xml
Synthesis 2016; 48(23): 4300-4304
DOI: 10.1055/s-0035-1561491
DOI: 10.1055/s-0035-1561491
paper
Protecting-Group-Free Total Synthesis of 8-Methoxygoniodiol
Weitere Informationen
Publikationsverlauf
Received: 07. Mai 2016
Accepted after revision: 09. Juni 2016
Publikationsdatum:
21. Juli 2016 (online)
![](https://www.thieme-connect.de/media/synthesis/201623/lookinside/thumbnails/ss-2016-z0324-op_10-1055_s-0035-1561491-1.jpg)
Abstract
A concise stereoselective total synthesis of the naturally occurring styryl lactone 8-methoxygoniodiol in five simple steps from readily available inexpensive trans-cinnamaldehyde is described. The efficient synthesis features a successful protecting-group-free strategy, with desirable step- and atom-economy. The synthetic strategy relies on a Maruoka asymmetric allylation, an epoxidation, a ring-closing metathesis, and a stereoselective epoxide ring opening as key steps.
Key words
lactones - methoxygoniodiol - natural products - total synthesis - Maruoka allylation - ring-closing metathesisSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561491.
- Supporting Information
-
References
- 1 Nicolaou KC, Vourloumis D, Winssinger N, Baran PS. Angew. Chem. Int. Ed. 2000; 39: 44
- 2 Wender PA, Verma VA, Paxton TJ, Pillow TH. Acc. Chem. Res. 2008; 41: 40
-
3 Trost BM. Science 1991; 254: 1471
- 4 From an interview with R. H. Grubbs, see: Stoddart A. Chem. World 2007; 4: C69
- 5a Hoffmann RW. Synthesis 2006; 3531
- 5b Young IS, Baran PS. Nat. Chem. 2009; 1: 193
- 5c Gaich T, Baran PS. J. Org. Chem. 2010; 75: 4657
- 5d Saicic RN. Tetrahedron 2014; 70: 8183
- 6a Argoudelis AD, Zieserl JF. Tetrahedron Lett. 1966; 1969
- 6b Wu Y, Shen X, Tang C.-J, Chen Z.-L, Hu Q, Shi W. J. Org. Chem. 2002; 67: 3802
-
6c Yamashita Y, Saito S, Ishitani H, Kobayashi S. J. Am. Chem. Soc. 2003; 125: 3793
- 6d Kobayashi S, Tsuchiya K, Harada T, Nishide M, Kurokawa T, Nakagawa T, Shimada N, Kobayashi K. J. Antibiot. 1994; 47: 697
- 7a Boucard V, Broustal G, Campagne JM. Eur. J. Org. Chem. 2007; 225 ; and references cited therein
- 7b Chen W.-Y, Wu C.-C, Lan Y.-S, Chang F.-R, Teng C.-M, Wu Y.-C. Eur. J. Pharmacol. 2005; 522: 20
- 7c Lewy DS, Gauss C.-M, Soenen DR, Boger DL. Curr. Med. Chem. 2002; 9: 2005
- 8a Buck SB, Hardouin C, Ichikawa S, Soenen DR, Gauss CM, Hwang I, Swingle MR, Bonness KM, Honkanen RE, Boger DL. J. Am. Chem. Soc. 2003; 125: 15694
- 8b Hoffmann HM. R, Rabe J. Angew. Chem. Int. Ed. 1985; 24: 94
- 9a Fang X.-P, Anderson JE, Chang C.-J, McLaughlin JL, Fanwick PE. J. Nat. Prod. 1991; 54: 1034
- 9b Goh SH, Ee GC. L, Chuah CH, Wei C. Aust. J. Chem. 1995; 48: 199
- 9c Wu Y.-C, Chang F.-R, Duh C.-Y, Wang S.-K, Wu T.-S. Phytochemistry 1992; 31: 2851
- 10 Kan WS. Pharmaceutical Botany . National Research Institute of Chinese Medicine; Taipei: 1979: 247
- 11a Lan Y.-H, Chang F.-R, Yu J.-H, Yang Y.-L, Chang Y.-L, Lee S.-J, Wu Y.-C. J. Nat. Prod. 2003; 66: 487
- 11b Lan Y.-H, Chang F.-R, Liaw C.-C, Wu C.-C, Chiang M.-Y, Wu Y.-C. Planta Med. 2005; 71: 153
- 12a Mondon M, Gesson J.-P. Curr. Org. Synth. 2006; 3: 41
- 12b Prasad KR, Gholap SL. J. Org. Chem. 2008; 73: 2916
- 12c Sabitha G, Bhikshapathi M, Ranjith N, Ashwini N, Yadav JS. Synthesis 2011; 821
- 12d Wouters AD, Bessa AB, Sachini M, Wessjohann LA, Lüdtke DS. Synthesis 2013; 45: 2222
- 13 Carreaux F, Favre A, Carboni B, Rouaud I, Boustie J. Tetrahedron Lett. 2006; 47: 4545
- 14 Yadav JS, Rao BM, Sanjeevrao K, Reddy BV. S. Synlett 2008; 1039
- 15 Kiran IN. C, Reddy RS, Suryavanshi G, Sudalai A. Tetrahedron Lett. 2011; 52: 438
- 16a Hanawa H, Hashimoto T, Maruoka K. J. Am. Chem. Soc. 2003; 125: 1708
- 16b Hanawa H, Uraguchi D, Konishi S, Hashimoto T, Maruoka K. Chem. Eur. J. 2003; 9: 4405
- 16c Ramesh P, Raju A, Fadnavis NW. Tetrahedron: Asymmetry 2015; 26: 1251
- 16d Ramesh P, Anjibabu R, Raju A. Tetrahedron Lett. 2016; 57: 2100
- 17a Johnson MR, Kishi Y. Tetrahedron Lett. 1979; 20: 4347
- 17b Kuppusamy S, Hasibur R, Pragna PD, Eswar B, Sridhar B, Mohapatra DK. Org. Lett. 2012; 14: 1082
- 18a Deiters A, Martin SF. Chem. Rev. 2004; 104: 2199
- 18b Trnka TM, Grubbs RH. Acc. Chem. Res. 2001; 34: 18
- 18c Grubbs RH, Miller SJ, Fu GC. Acc. Chem. Res. 1995; 28: 446
- 18d Hoveyda AH, Zhugralin AR. Nature 2007; 450: 243
- 18e Ramesh P, Raju A, Paramesh J, Ramisetti A. Tetrahedron Lett. 2016; 57: 1087
- 19a Dalpozzo R, Nardi M, Oliverio M, Paonessa R, Procopio A. Synthesis 2009; 3433
- 19b Uesugi S.-i, Watanabe T, Imaizumi T, Shibuya M, Kanoh N, Iwabuchi Y. Org. Lett. 2014; 16: 4408
- 19c Williams DB. G, Lawton M. Org. Biomol. Chem. 2005; 3: 3269
- 19d Izquierdo J, Rodrıguez S, González FV. Org. Lett. 2011; 13: 3856
- 19e Venkatasubbaiah K, Zhu X, Kays E, Hardcastle KI, Jones CW. ACS Catal. 2011; 1: 489
- 19f Wang C, Yamamoto H. J. Am. Chem. Soc. 2014; 136: 6888