Total synthesis of cis-reticulatacin-10-ones A and B: absolute stereochemical assignment
Total synthesis of cis-reticulatacin-10-ones A and B: absolute stereochemical assignment
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).
4543-4545
Abdel Ghani, Sherif B.
9b8b6bd8-47cd-4268-bfb3-4de0677fb896
Brown, Lynda J.
75aa95fa-5d27-46a7-9dbe-0f465a664f5b
Figadère, Bruno
a2e2bc0e-7a42-4ca2-86bf-41dab616aeea
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5
October 2010
Abdel Ghani, Sherif B.
9b8b6bd8-47cd-4268-bfb3-4de0677fb896
Brown, Lynda J.
75aa95fa-5d27-46a7-9dbe-0f465a664f5b
Figadère, Bruno
a2e2bc0e-7a42-4ca2-86bf-41dab616aeea
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5
Abdel Ghani, Sherif B., Brown, Lynda J., Figadère, Bruno and Brown, Richard C.D.
(2010)
Total synthesis of cis-reticulatacin-10-ones A and B: absolute stereochemical assignment.
Organic & Biomolecular Chemistry, 8 (20), .
(doi:10.1039/C0ob00259c).
(PMID:20733975)
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).
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Published date: October 2010
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Local EPrints ID: 180735
URI: http://eprints.soton.ac.uk/id/eprint/180735
ISSN: 1477-0520
PURE UUID: b76c36d2-88f4-40bf-a188-649ce0ac7fc7
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Date deposited: 13 Apr 2011 08:35
Last modified: 15 Mar 2024 02:59
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Author:
Sherif B. Abdel Ghani
Author:
Bruno Figadère
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