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 2015; 26(18): 2485-2490
DOI: 10.1055/s-0035-1560635
DOI: 10.1055/s-0035-1560635
synpacts
The Biosynthesis and Biomimetic Synthesis of Merochlorins A and B
Further Information
Publication History
Received: 27 July 2015
Accepted after revision: 04 September 2015
Publication Date:
30 September 2015 (online)
Abstract
The interplay between biosynthetic studies and biomimetic synthesis is discussed in the context of the merochlorin family of marine natural products. Total syntheses of merochlorin A by our group and merochlorin B by the Trauner group are presented alongside the biosynthetic studies of Moore and co-workers. The common theme is the generation of complex polycyclic ring systems by oxidative dearomatization–cyclization cascade reactions.
-
References
- 1a Kaysser L, Bernhardt P, Nam S.-J, Loesgen S, Ruby JG, Skewes-Cox P, Jensen PR, Fenical W, Moore BS. J. Am. Chem. Soc. 2012; 134: 11988
- 1b Sakoulas G, Nam S.-J, Loesgen S, Fenical W, Jensen PR, Nizet V, Hensler M. PLoS One 2012; 7: e29439
- 2 Pepper HP, George JH. Angew. Chem. Int. Ed. 2013; 52: 12170
- 3 Meier R, Strych S, Trauner D. Org. Lett. 2014; 16: 2634
- 4a Zhuo C.-X, Zhang W, You S.-L. Angew. Chem. Int. Ed. 2012; 51: 12662
- 4b Roche SP, Porco JA. Jr. Angew. Chem. Int. Ed. 2011; 50: 4068
- 4c Jackson SK, Wu K.-L, Pettus TR. R In Biomimetic Organic Synthesis . Vol. 2. Poupon E, Nay B. Wiley-VCH; Weinheim: 2011: 723-749
- 4d Pouysegu L, Deffieux D, Quideau S. Tetrahedron 2010; 66: 2235
- 4e Quideau S, Pouysegu L, Deffieux D. Synlett 2008; 467
- 5 Teufel R, Kaysser L, Villaume MT, Diethelm S, Carbullido MK, Baran PS, Moore BS. Angew. Chem. Int. Ed. 2014; 53: 11019
- 6a Bernhardt P, Okino T, Winter JM, Miyanaga A, Moore BS. J. Am. Chem. Soc. 2011; 133: 4268
- 6b Winter JM, Moore BS. J. Biol. Chem. 2009; 284: 18577
- 7 Biber N, Möws K, Plietker B. Nat. Chem. 2011; 3: 938
- 8 For a related use of Pb(OAc)4 to induce oxidative dearomatization, see: Green JC, Pettus TR. R. J. Am. Chem. Soc. 2011; 133: 1603
- 9 Bernard AM, Ghiani MR, Piras PP, Rivoldini A. Synthesis 1989; 287
- 10a Gembus V, Poisson T, Oudeyer S, Marsais F, Levacher V. Synlett 2009; 2437
- 10b Andrey O, Glanzmann C, Landais Y, Parra-Rapado L. Tetrahedron 1997; 53: 2835
- 11 Beekman AM, Martinez EC, Barrow RA. Org. Biomol. Chem. 2013; 11: 1109
- 12 Mani NS, Jablonowski JA, Jones TK. J. Org. Chem. 2004; 69: 8115
- 13a Koser GF, Wettach RH, Troup JM, Frenz BA. J. Org. Chem. 1976; 41: 3609
- 13b Moriarty RM, Vaid RK, Koser GF. Synlett 1990; 365
- 14 Diethelm S, Teufel R, Kaysser L, Moore BS. Angew. Chem. Int. Ed. 2014; 53: 11023
- 15 Pittelkow M, Boas U, Christensen JB. Org. Lett. 2006; 8: 5817
- 16 Kimura M, Fukasaka M, Tamaru Y. Synthesis 2006; 3611
- 17 For a recent perspective on the benefits of a biomimetic approach to natural product synthesis, see: Razzak M, De Brabander JK. Nat. Chem. Biol. 2011; 7: 865
For recent reviews of oxidative dearomatization reactions in natural product synthesis, see: