Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2013; 24(2): 157-160
DOI: 10.1055/s-0032-1317848
DOI: 10.1055/s-0032-1317848
letter
A Concise Total Synthesis of the Purported Structure of Flossonol
Further Information
Publication History
Received: 03 September 2012
Accepted after revision: 15 November 2012
Publication Date:
21 December 2012 (online)
Abstract
We report the first total synthesis of flossonol in only five steps and of one of its isomers in seven steps using a radical addition/cyclization sequence as the key step. Comparison of our spectroscopic data with those of the literature indicates a misassignment in the structure of flossonol.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
-
References
- 1 Sun N, Chang C, Cassady JM. Phytochemistry 1987; 26: 3051
- 2 Geran RI, Greenberg NH, MacDonald MM, Schumacher AM, Abbott BJ. Cancer Chemother. 1972; 3: 1
- 3a Hernandez-Romero Y, Rojas JI, Castillo R, Rojas A, Mata R. J. Nat. Prod. 2004; 67: 160
- 3b Tezuka Y, Morikawa K, Li F, Auw L, Awale S, Nobukawa T, Kadota S. J. Nat. Prod. 2011; 74: 102
- 3c Park BM, Hong SS, Lee C, Lee MS, Kang SJ, Shin YS, Jung JK, Hong JT, Kim Y, Lee MK, Hwang BY. Arch. Pharm. Res. 2010; 33: 381
- 3d Messiano GB, Silva T, Nascimento IR, Lopes LM. X. Phytochemistry 2009; 70: 590
- 4a Haworth RD. J. Chem. Soc. 1932; 1125
- 4b Esteban G, Lopez-Sanchez M, Martinez ME, Plumet J. Tetrahedron 1998; 54: 197
- 4c Caro Y, Masaguer CF, Ravina E. Tetrahedron: Asymmetry 2003; 14: 381
- 4d Cui DM, Kawamura M, Shimada S, Hayashi T, Tanaka M. Tetrahedron Lett. 2003; 44: 4007
- 5a Heiba EI, Dessau RM. J. Am. Chem. Soc. 1972; 94: 2888
- 5b Russel GA, Kulkarni SV, Khanna RK. J. Org. Chem. 1990; 55: 1080
- 5c Snider BB, Kwon T. J. Org. Chem. 1990; 55: 4786
- 5d Russell GA, Chen P, Kim BH, Rajaratnam R. J. Am. Chem. Soc. 1997; 119: 8795
- 6a Liard A, Quiclet-Sire B, Zard SZ. Tetrahedron Lett. 1997; 38: 1759
- 6b Cordero-Vargas A, Pérez-Martin I, Quiclet-Sire B, Zard SZ. Org. Biomol. Chem. 2004; 2: 3018
- 6c Petit L, Zard SZ. Chem. Commun. 2010; 46: 5148
- 6d Cordero-Vargas A, Quiclet-Sire B, Zard SZ. Org. Lett. 2003; 5: 3717
- 7 Pretsch E, Clerc T, Seibl J, Simon W. Tabellen zur Strukturaufklärung organischer Verbindungen mit spektroskopischen Methoden. Springer-Verlag; Berlin: 1986