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Synthesis 2013; 45(5): 673-677
DOI: 10.1055/s-0032-1318141
DOI: 10.1055/s-0032-1318141
paper
Stereoselective Synthesis of the C10–C18 Fragment of Iriomoteolide-3a
Further Information
Publication History
Received: 26 October 2012
Accepted after revision: 09 January 2013
Publication Date:
07 February 2013 (online)
Abstract
An efficient synthesis of the highly stereogenic centered C10–C18 fragment of iriomoteolide-3a has been accomplished. Key steps include Sharpless asymmetric dihydroxylation and epoxidation for generation of the desired stereocenters.
Key words
macrolide - total synthesis - iriomoteolide-3a - ortho-Claisen rearrangement - Sharpless dihydroxylationSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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References
- 1 Oguchi K, Tsuda M, Iwamoto R, Okamoto Y, Kobayashi J, Fukushi E, Kawabata J, Ozawa T, Masuda A, Kitaya Y, Omasa K. J. Org. Chem. 2008; 73: 1567
- 2 Cribiú R, Jäger C, Nevado C. Angew. Chem. Int. Ed. 2009; 48: 8780
- 3 Reddy ChR, Dharmapuri G, Rao NN. Org. Lett. 2009; 11: 5730
- 4 Zhang Y, Deng L, Zhao G. Org. Biomol. Chem. 2011; 9: 4518
- 5 Chang C.-Y. J. Chin. Chem. Soc. 2011; 58: 31
- 6a Reddy ChR, Rao NN. Tetrahedron Lett. 2009; 50: 2478
- 6b Reddy ChR, Rao NN. RSC Adv. 2012; 2: 7724
- 6c Reddy ChR, Rao NN. Eur. J. Org. Chem. 2012; 1819
- 6d Reddy ChR, Suman D, Rao NN. Synlett 2012; 23: 272
- 7a Singh OV, Han H. Org. Lett. 2007; 9: 4801
- 7b Lee AH. F, Chan AS. C, Li T. Tetrahedron 2003; 59: 833
- 8 Sinha SC, Bagchi AS, Keinan E. J. Am. Chem. Soc. 1995; 117: 1447
- 9a Evans AP, Roseman JD. Tetrahedron Lett. 1997; 38: 5249
- 9b Mandel AL, Bellosta V, Curran DP, Cossy J. Org. Lett. 2009; 11: 3282
- 10 Compound 13 was converted into a known compound 13a (Scheme 3). A comparison of specific rotations {observed for 13a: [α]D 30 +16.3 (c 1.0, CHCl3), Lit.3: [α]D 30 +16.6 (c 1.0, CHCl3)} showed that the enantiomeric excess in the Sharpless dihydroxylation was >95%, and also confirmed the exclusive formation of 13 from 12 (by NOE studies on 13a 12).
- 11 Mohapatra DK, Sahoo G, Sankar K, Gurjar MK. Tetrahedron: Asymmetry 2008; 19: 2123
- 12 NOE experiments were carried out on compound 13a and the enhancements are shown in Figure 2.
- 13 Reddy ChR, Rao NN. Tetrahedron Lett. 2010; 51: 5840
- 14 Munakata R, Katakai H, Ueki T, Kurosaka J, Takao KI, Tadano KI. J. Am. Chem. Soc. 2004; 126: 11254
- 15 Parikh JR, Doering WV. E. J. Am. Chem. Soc. 1967; 89: 5505