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Thursday 27 August 2015

30(S)-hydroxybullatacin

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Total synthesis of 30(S)-hydroxybullatacin

In 2003, Marshall’s group disclosed a modular synthetic approach to the adjacent bis-THF rings (Scheme 46) [108]. This approach featured highly selective additions of chiral R-oxygenated allylic stannane and indium reagents such as B1 and D1 (M = SnBu3 or InBr2) to an acylic core aldehyde precursor (A1 then C1) followed by core ring closure (E1F1) and ensuing Sonogashira coupling (F1 + G1H1) to append the butenolide segment. This straightforward strategy permitted the efficient assembly of the acetogenin structure from four basic subunits. By interchanging these subunits a variety of natural acetogenins and their isomers should be accessible in relatively few steps. They extended the scope of their modular four-component synthesis of annonaceous acetogenins to 30(S)-hydroxybullatacin (335). The 1H and 13C NMR spectra of the tetraol product 335 were in complete agreement with the reported spectra [109].


Reference 109

109.Gu, Z.-M.; Zeng, L.; Schwedler, J. T.; Wood, K. V.; McLaughlin, J. L. Phytochemistry 1995, 40, 467–477. doi:10.1016/0031-9422(95)00308-T
Go to reference 109


Abstract Image
A synthesis of the bistetrahydrofuran Annonaceous acetogenins 30(S)-hydroxybullatacin, uvarigrandin A, and 5(R)-uvarigrandin A through application of a previously disclosed four-component modular approach is described in which extended core segments are coupled to a C4- or C5-hydroxy butenolide terminus. The butenolide termini segments were prepared from (S)- or (R)-malic acid. Spectral properties of synthetic 30(S)-hydroxybullatacin and uvarigrandin A, as well as their Mosher ester derivatives, were in close agreement to the reported values for the natural substances. The synthetic 5(R)-uvarigrandin A is possibly identical to narumicin I, but subtle differences in the reported NMR spectra prevented an unambiguous assessment of this point.
 http://pubs.acs.org/doi/abs/10.1021/jo0266137?journalCode=joceah


 nmr seehttp://pubs.acs.org/doi/suppl/10.1021/jo0266137/suppl_file/jo0266137_s.pdf

Recent progress on the total synthesis of acetogenins from Annonaceae

Nianguang Li1, Zhihao Shi2, Yuping Tang3, Jianwei Chen1 and Xiang Li1Email of corresponding author
1Department of Medicinal Chemistry, Nanjing University of Chinese Medicine, No. 138, Xianlindadao, Nanjing, Jiangsu 210046, P. R. China. Tel & Fax: +86-25-85811512
2Division of Organic Chemistry, China Pharmaceutical University, Nanjing, Jiangsu 211198, P. R. China
3Jiangsu Key Laboratory for TCM Formulae Research, Nanjing University of Chinese Medicine, Nanjing, Jiangsu 210046, P. R. China.
Email of corresponding author Corresponding author email     
Beilstein J. Org. Chem. 2008, 4, No. 48.

 http://www.beilstein-journals.org/bjoc/single/articleFullText.htm?publicId=1860-5397-4-48

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