A triple-aldol cascade reaction for the rapid assembly of polyketides
- PMID: 20229553
- PMCID: PMC3066012
- DOI: 10.1002/anie.200907076
A triple-aldol cascade reaction for the rapid assembly of polyketides
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References
-
- Mukaiyama T, Narasaka K, Banno K. Chem. Lett. 1973:1011–1014.
- Kato J, Mukaiyama T. Chem. Lett. 1983:1727–1728.
- Kohler BAB. Synth. Commun. 1985;15:39–42.
-
-
For cross-aldol reactions, see: Mukaiyama T. Organic Reactions. Vol. 28. New York: Wiley; 1982. pp. 203–331. Heathcock CK, Kim BM, Williams SF, Masamune S, Rathke MW, Weipert P, Paterson I. Comprehensive Organic Synthesis. Vol. 2. Oxford: Pergamon; 1991. pp. 133–319. Nelson SG. Tetrahedron: Asymmetry. 1998;9:357–389. Mahrwald R. Chem. Rev. 1999;99:1095–1120. Denmark SE, Ghosh SK. Angew. Chem. 2001;113:4895–4898. Angew. Chem. Int. Ed. 2001;40:4759–4762. Northrup AB, MacMillan DWC. J. Am. Chem. Soc. 2002;124:6798–6799. Denmark SE, Bui T. J. Org. Chem. 2005;70:10190–10193. Iwata M, Yazaki R, Suzuki Y, Kumagai N, Shibasaki M. J. Am. Chem. Soc. 2009;131:18244–18245..
-
-
-
For the allylation of aldehydes, see: Fleming I. In: Comprehensive Organic Synthesis. Trost BM, editor. Vol. 2. Oxford: Pergamon; 1991. pp. 563–593. Yamamoto Y, Asao N. Chem. Rev. 1993;93:2207–2293. Denmark SE, Fu J. Chem. Rev. 2003;103:2763–2793..
-
-
- Gijsen HJM, Wong C-H. J. Am. Chem. Soc. 1995;117:7585–7591.
- Yun S-S, Suh I-H, Choi S-S, Lee S. Chem. Lett. 1998:985–986.
- Haeuseler A, Henn W, Schmittel M. Synthesis. 2003:2576–2589.
- Casas J, Engqvist M, Ibrahem I, Kaynak B, Córdova A. Angew. Chem. 2005;117:1367–1369. - PubMed
- Angew. Chem. Int. Ed. 2005;44:1343–1345. - PubMed
- Wang X, Meng Q, Perl NR, Xu Y, Leighton JL. J. Am. Chem. Soc. 2005;127:12806–12807. - PubMed
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