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Issue 20, 2010
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Total synthesis of cis-reticulatacin-10-ones A and B: absolute stereochemical assignment

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Abstract

cis-Reticulatacin-10-ones A and B were synthesised as a predefined mixture of diastereoisomers (dr ∼ 1 : 9) in nine steps from the acid chloride 8, and without the use of hydroxyl protecting groups. Comparison of the chiral HPLC chromatogram of the synthetic sample with that of the natural product isolated from the roots of the tropical fruit tree Annona muricata L. showed the natural product to be a mixture of A and B diastereoisomers (dr ∼ 1 : 1).

Graphical abstract: Total synthesis of cis-reticulatacin-10-ones A and B: absolute stereochemical assignment

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Publication details

The article was received on 15 Jun 2010, accepted on 14 Jul 2010 and first published on 23 Aug 2010


Article type: Communication
DOI: 10.1039/C0OB00259C
Citation: Org. Biomol. Chem., 2010,8, 4543-4545
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    Total synthesis of cis-reticulatacin-10-ones A and B: absolute stereochemical assignment

    S. B. Abdel Ghani, L. J. Brown, B. Figadère and R. C. D. Brown, Org. Biomol. Chem., 2010, 8, 4543
    DOI: 10.1039/C0OB00259C

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