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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
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).
1477-0520
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
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), 4543-4545. (doi:10.1039/C0ob00259c). (PMID:20733975)

Record type: Article

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

Identifiers

Local EPrints ID: 180735
URI: http://eprints.soton.ac.uk/id/eprint/180735
ISSN: 1477-0520
PURE UUID: b76c36d2-88f4-40bf-a188-649ce0ac7fc7
ORCID for Lynda J. Brown: ORCID iD orcid.org/0000-0002-5678-0814
ORCID for Richard C.D. Brown: ORCID iD orcid.org/0000-0003-0156-7087

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Date deposited: 13 Apr 2011 08:35
Last modified: 20 Jul 2019 01:16

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Contributors

Author: Sherif B. Abdel Ghani
Author: Lynda J. Brown ORCID iD
Author: Bruno Figadère

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