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 2013; 45(8): 1034-1038
DOI: 10.1055/s-0032-1316861
DOI: 10.1055/s-0032-1316861
paper
Concise Total Synthesis of Helicascolides A, B, and C
Weitere Informationen
Publikationsverlauf
Received: 15. Dezember 2012
Accepted after revision: 05. Februar 2013
Publikationsdatum:
14. März 2013 (online)
Abstract
The concise total synthesis of helicascolides A, B, and C has been achieved in seven steps starting from commercially available tiglic aldehyde [(E)-2,3-dimethylacrylaldehyde]. Oppolzer’s sultam aldol, Mukaiyama aldol, and Dess–Martin periodinane oxidation reactions are the key steps involved in the target synthesis.
Key words
helicascolides A, B, and C - lactones - antifungal agents - asymmetric aldol reactions - total synthesisSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1a Ishigami K. Biosci., Biotechnol., Biochem. 2009; 73: 971
- 1b Nicolaou KC, Chen JS, Dalby SM. Bioorg. Med. Chem. 2009; 17: 2290
- 1c Piel J. Nat. Prod. Rep. 2009; 26: 338
- 1d Riatto VB, Pilli RA, Victor MM. Tetrahedron 2008; 64: 2279
- 1e Greve H, Schupp PJ, Eguereva E, Kehraus S, König GM. J. Nat. Prod. 2008; 71: 1651
- 1f Ferraz HM. C, Bombonato FI, Longo Jr LS. Synthesis 2007; 21: 3261
- 1g Surat B, Prasat K, Masahiko I, Daraporn P, Morakot T, Yodhathai T. J. Nat. Prod. 2001; 64: 965
- 1h Faulkner DJ. Nat. Prod. Rep. 2002; 19: 1; and references cited therein
- 2a Hoffman HM. R, Rabe J. Angew. Chem., Int. Ed. Engl. 1985; 24: 94
- 2b Collins I. J. Chem. Soc., Perkin Trans. 1 1999; 1377
- 2c Yasui K, Tamura Y, Nakatani T, Kawada K, Ohtani M. J. Org. Chem. 1995; 60: 7567; and references cited therein
- 2d Drewes SE, Sehlapelo BM, Horn MM, Scott-Shaw R, Sandor P. Phytochemistry 1995; 38: 1427
- 2e Li H.-J, Lin Y.-C, Yao J.-H, Vrijmoed LL. P, Gareth Jones EB. J. Asian Nat. Prod. Res. 2004; 6: 185
- 2f Bermejo A, Blazquez MA, Sundar rao K. Phytochemistry 1998; 47: 1375
- 2g Sturgeon CM, Cinel B, Diaz-Marrero AR, McHardy LM, Ngo M, Andersen RJ, Roberge M. Cancer Chemother. Pharmacol. 2008; 61: 407
- 2h Verzár R, Petri G. J. Ethnopharmacol. 1987; 19: 67
- 3a Blunt JW, Copp BR, Munro MH. G, Northcote PT, Prinsep MR. Nat. Prod. Rep. 2004; 21: 1
- 3b Fenical W, Jensen PR In Marine Biotechnology. Vol. I. Attawas DH, Zaborsky OK. Plenum; New York: 1993: 419-457
- 4a Fujii Y, Fukuda A, Hamasaki T, Ichimoto I, Nakajima H. Phytochemistry 1995; 40: 1443
- 4b Dai H.-Q, Kang Q.-J, Li G.-H, Shen Y.-M. Helv. Chim. Acta 2006; 89: 527
- 4c Jaduco R, Proksch P, Wray V, Sudarsono AB, Graefe U. J. Nat. Prod. 2001; 64: 527
- 5 Carlos J.-R, Eduardo O.-B, Arnold AE, Luis C.-R. Pharm. Biol. 2008; 46: 1
- 6 Hein SM, Gloer JB, Koster B, Malloch D. J. Nat. Prod. 2001; 64: 809
- 7 Boonphong S, Kittakoop P, Isaka M, Pittayakhajonwut D, Tanticharoen M, Thebtaranonth Y. J. Nat. Prod. 2001; 64: 965
- 8 Tsuda M, Mugishima T, Komatsu K, Sone T, Tanaka M, Mikami Y, Kobayashi J. J. Nat. Prod. 2003; 66: 412
- 9 Poch GK, Gloer JB. J. Nat. Prod. 1989; 52: 257
- 10 Tarman K, Palm GJ, Porzel A, Merzweiler K, Arnold N, Wessjohann LA, Unterseher M, Lindequist U. Phytochem. Lett. 2012; 5: 83
- 11a Yadav JS, Mandal SS. Tetrahedron Lett. 2011; 52: 5747
- 11b Yadav JS, Mandal SS, Reddy JS. S, Srihari P. Tetrahedron 2011; 67: 4620
- 11c Yadav JS, Reddy JS. S, Mandal SS, Srihari P. Synlett 2010; 2636
- 11d Srihari P, Kumaraswamy B, Rao GM, Yadav JS. Tetrahedron: Asymmetry 2010; 21: 106
- 11e Srihari P, Bhasker EV, Reddy AB, Yadav JS. Tetrahedron Lett. 2009; 50: 2420
- 11f Yadav JS, Kumar VN, Rao RS, Srihari P. Synthesis 2008; 1938
- 11g Srihari P, Kumar BP, Subbarayudu K, Yadav JS. Tetrahedron Lett. 2007; 48: 6977
- 11h Srihari P, Bhasker EV, Harshavardhan SJ, Yadav JS. Synthesis 2006; 4041
- 12 Radha Krishna P, Mallula VS, Arun Kumar PV. Tetrahedron Lett. 2012; 53: 4997
- 13a Yadav JS, Rajender V. Eur. J. Org. Chem. 2010; 2148
- 13b Oppolzer W, Starkemann C, Rodriguez I, Bernardinelli G. Tetrahedron Lett. 1991; 32: 61
- 13c Oppolzer W, Lienard P. Tetrahedron Lett. 1993; 34: 4321
- 13d Kumaraswamy G, Padmaja M, Markondaiah B, Nivedita J, Sridhar B, Udaya Kiran M. J. Org. Chem. 2006; 71: 337
- 14a Yadav JS, Ganganna B, Bhunia DC. Synthesis 2012; 44: 1365
- 14b Srihari P, Satyanarayana K, Ganganna B, Yadav JS. J. Org. Chem. 2011; 76: 1922
- 15 Yadav JS, Padmavani B, Venugopal C. Tetrahedron Lett. 2009; 50: 3772
- 16 Kiyooka S.-I, Shiinoki M, Nakata K, Goto F. Tetrahedron Lett. 2002; 43: 5377
- 17 Oisaki K, Suto Y, Kanai M, Shibasaki M. J. Am. Chem. Soc. 2003; 125: 5644
- 18 Srihari P, Prem Kumar B, Subbarayudu K, Yadav JS. Tetrahedron Lett. 2007; 48: 6977
For our contributions on lactone-containing molecules, see: