Issue 20, 2010
From the journal:

Organic & Biomolecular Chemistry

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

Sherif B. Abdel Ghani,a   Lynda J. Brown,b   Bruno Figadèrec  and  Richard C. D. Brown*b  

* Corresponding authors

a Plant Protection Department, Faculty of Agriculture, Ain Shams University, Hadayek Shoubra 11241, Cairo, Egypt

b School of Chemistry, University of Southampton, Highfield, Southampton, UK
E-mail: rcb1@soton.ac.uk
Fax: +44-(0)23-8058-6805
Tel: +44-(0)23-8059-4108

c Laboratoire de Pharmacognosie, associé au CNRS (BioCIS), Université Paris-Sud, Faculté de Pharmacie, Rue J-B Clément, Chatenay-Malabry, France

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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Article information

DOI
https://doi.org/10.1039/C0OB00259C
Article type
Communication
Submitted
15 Jun 2010
Accepted
14 Jul 2010
First published
23 Aug 2010

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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