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Efficient, Divergent Synthesis of Cryptophycin Unit A Analogues

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Specialty Chemistry
Date 2012 May 24
PMID 22617820
Citations 5
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Abstract

A flexible and divergent synthesis of cryptophycin unit A analogues is described. This method relies on iridium-catalysed stereo- and enantioselective crotylation and chemoselective one-pot oxidative olefination to access common intermediate . Heck, cross metathesis, and Suzuki-Miyaura reactions are illustrated for the generation of methyl ester unit A analogues .

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References
1.
Varie D, Shih C, Hay D, Andis S, Corbett T, Gossett L . Synthesis and biological evaluation of cryptophycin analogs with substitution at C-6 (fragment C region). Bioorg Med Chem Lett. 1999; 9(3):369-74. DOI: 10.1016/s0960-894x(98)00748-3. View

2.
Ding Y, Rath C, Bolduc K, Hakansson K, Sherman D . Chemoenzymatic synthesis of cryptophycin anticancer agents by an ester bond-forming non-ribosomal peptide synthetase module. J Am Chem Soc. 2011; 133(37):14492-5. PMC: 3174474. DOI: 10.1021/ja204716f. View

3.
Hoye T, Jeffrey C, Shao F . Mosher ester analysis for the determination of absolute configuration of stereogenic (chiral) carbinol carbons. Nat Protoc. 2007; 2(10):2451-8. DOI: 10.1038/nprot.2007.354. View

4.
Beck Z, Aldrich C, Magarvey N, Georg G, Sherman D . Chemoenzymatic synthesis of cryptophycin/arenastatin natural products. Biochemistry. 2005; 44(41):13457-66. DOI: 10.1021/bi051140u. View

5.
Eggen M, Georg G . The cryptophycins: their synthesis and anticancer activity. Med Res Rev. 2002; 22(2):85-101. DOI: 10.1002/med.10002. View