Studies toward the synthesis of maoecrystal V
- PMID: 21271687
- PMCID: PMC3373731
- DOI: 10.1021/ol1031238
Studies toward the synthesis of maoecrystal V
Abstract
An approach toward the synthesis of maoecrystal V is described. The synthetic strategy for this approach was designed to address unique challenges posed by the strained tetrahydrofuran ring at the center of the target structure.
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References
-
- Li S-H, Wang J, Niu X-M, Shen Y-H, Zhang H-J, Sun H-D, Li M-L, Tian Q-E, Lu Y, Cao P, Zheng Q-T. Org Lett. 2004;6:4327–4330. - PubMed
-
- Gong J, Lin G, Li C-C, Yang Z. Org Lett. 2009;11:4770–4773. - PubMed
- Krawczuk PJ, Schöne N, Baran PS. Org Lett. 2009;11:4774–4776. - PMC - PubMed
- Peng F, Yu M, Danishefsky SJ. Tetrahedron Lett. 2009;50:6586–6587. - PMC - PubMed
- Nicolaou KC, Dong L, Deng L, Talbot AC, Chen DY-K. Chem Commun. 2010;46:70–72. - PubMed
- Lazarski KE, Hu DX, Stern CL, Thomson RJ. Org Lett. 2010;12:3010–3013. - PMC - PubMed
- Baitinger I, Mayer P, Trauner D. Org Lett. 2010;12:5656–5659. - PubMed
-
- Gong J, Lin G, Sun W, Li C-C, Yang Z. J Am Chem Soc. 2010;132:16745–16746. - PubMed
-
-
For recent examples using masked ortho-quinone as substrates for Diels–Alder reactions, see: Chu C-S, Lee T-H, Rao PD, Song L-D, Liao C-C. J Org Chem. 1999;64:4111–4118.Nicolaou KC, Toh Q-Y, Chen DY-K. J Am Chem Soc. 2008;130:11292–11293.Singh V, Bhalerao P, Mobin SM. Tetrahedron Lett. 2010;51:3337–3339.
-
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