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Synlett 2019; 30(02): 178-180
DOI: 10.1055/s-0037-1609657
DOI: 10.1055/s-0037-1609657
letter
Synthesis of the Proposed Structure of Cryptoconcatone H
We thank Nanyang Technological University for support of this work.Further Information
Publication History
Received: 10 October 2018
Accepted after revision: 05 November 2018
Publication Date:
11 December 2018 (online)
Abstract
A synthesis of the proposed structure of cryptoconcatone H and one diastereoisomer has been achieved, featuring a tandem deprotection–oxa-Michael addition to establish the tetrahydropyran moiety. Comparison of the NMR spectroscopic data confirms that the original structural assignment was incorrect.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609657.
- Supporting Information
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References
- 1 Yang B.-Y, Kong L.-Y, Wang X.-B, Zhang Y.-M, Li R.-J, Yang M.-H, Luo J.-G. J. Nat. Prod. 2016; 79: 196
- 2a Bates RW, Wang K, Zhou G, Kang DZ. Synlett 2015; 26: 751
- 2b Bates RW, Lek TG. Synthesis 2014; 46: 1731
- 2c Bates RW, Song P. Synthesis 2010; 2935
- 3a Nasir NM, Ermanis K, Clarke PA. Org. Biomol. Chem. 2012; 12: 3323
- 3b Fuwa H. Heterocycles 2012; 86: 1255
- 3c Nising CF, Bräse S. Chem. Soc. Rev. 2012; 41: 988
- 3d Larossa I, Romea P, Urpí F. Tetrahedron 2008; 64: 2683
- 3e Clarke PA, Santos S. Eur. J. Org. Chem. 2006; 2045
- 3f Hu J, Bian M, Ding H. Tetrahedron Lett. 2016; 57: 5519
- 4 Della-Felice F, Sarotti AM, Pilli RA. J. Org. Chem. 2017; 82: 9191
- 5 For a discussion of recent trends in structural revision, see: Chhetri BK, Lavoie S, Sweeney-Jones AM, Kubanek J. Nat. Prod. Rep. 2018; 35: 514
- 6 Crimmins MT, Christie HS, Hughes CO. Org. Synth. 2011; 88: 364
- 7 Yadav JS, Ganganna B, Bhunia DC. Synthesis 2012; 44: 1365
- 8 Crimmins MT, King BW, Tabet EA, Chaudhary K. J. Org. Chem. 2001; 66: 894
- 9 Evans DA, Chapman KT, Carreira EM. J. Am. Chem. Soc. 1988; 110: 3560
- 10 Only a trace of cinnamaldehyde could be detected in the reaction mixture.
- 11 For another example of tandem deprotection–cyclisation, see: Paterson I, Haslett GW. Org. Lett. 2013; 15: 1338
- 12 See Supporting Information for more details.
- 13 For examples, see: Podlech J, Maier TC. Synthesis 2003; 633 ; for an additional example, see ref. 2b
- 14 Keck GE, Tarbet KH, Geraci LS. J. Am. Chem. Soc. 1993; 115: 8467
- 15 Wang G, Krische MJ. J. Am. Chem. Soc. 2016; 138: 8088
For some recent examples from this laboratory, see:
For reviews, see:
For a partial review, see: