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Synthesis 2014; 46(22): 3041-3046
DOI: 10.1055/s-0034-1378557
DOI: 10.1055/s-0034-1378557
paper
A Concise Total Synthesis of (±)-Cassumunin C
Weitere Informationen
Publikationsverlauf
Received: 11. Juni 2014
Accepted after revision: 11. Juli 2014
Publikationsdatum:
14. August 2014 (online)

Abstract
The first concise and efficient total synthesis of (±)-cassumunin C has been accomplished with a longest linear sequence of seven steps in 11.7% yield. The key steps involve aromatic propargylation and stereoselective reduction of alkynylphenol to the corresponding (E)-alkenylphenol.
Key words
aldol condensation - aromatic propargylation - Reimer–Tiemann reaction - lithium aluminum hydride - natural productSupporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
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References
- 1a Ruby AJ, Kuttan G, Babu KD, Rajasekharan KN, Kuttan R. Cancer Lett. 1995; 94: 79
- 1b Aggarwal BB, Kumar A, Bharti AC. Anticancer Res. 2003; 23: 363
- 1c Lopresti AL, Hood SD, Drummond PD. J. Psychopharmacol. 2012; 26: 1512
- 1d Bairwa K, Grover J, Kania M, Jachak SM. RSC Adv. 2014; 4: 13946
- 2 Osawa T, Sugiyama Y, Inayoshi M, Kawakishi S. Biosci., Biotechnol., Biochem. 1995; 59: 1609
- 3 Masuda T, Jitoe A, Nobuji N. Chem. Lett. 1993; 189
- 4 Masuda T, Jitoe A. J. Agric. Food Chem. 1994; 42: 1850
- 5 Masuda T, Matsumura H, Oyama Y, Takeda Y, Jitoe A, Kida A, Hidaka K. J. Nat. Prod. 1998; 61: 609
- 6 Bhattacharya AK, Kaur T, Ganesh KN. Synthesis 2010; 1141
- 7a Nishibayashi Y, Yoshikawaa M, Inada Y, Hidai M, Uemura S. J. Am. Chem. Soc. 2002; 124: 11846
- 7b Georgy M, Boucard V, Campagne JM. J. Am. Chem. Soc. 2005; 127: 14180
- 7c Kennedy-Smith JJ, Young LA, Toste FD. Org. Lett. 2004; 6: 1325
- 8 Srihari P, Bhunia DC, Sreedhar P, Mandal SS, Reddy JS. S, Yadav JS. Tetrahedron Lett. 2007; 48: 8120
- 9 Sonnet PE. Tetrahedron 1979; 36: 557
- 10 Bai XF, Xu LW, Zheng LS, Jiang JX, Lai GQ, Shang JY. Chem. Eur. J. 2012; 18: 8174
- 11a Rossi R, Carpita A. Synthesis 1977; 561
- 11b Rao AV. R, Reddy SP, Reddy ER. J. Org. Chem. 1986; 51: 4158
- 11c Denmark SE, Werner NS. J. Am. Chem. Soc. 2008; 130: 16382