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Total synthesis and stereochemical assignment of cis-uvariamicin I and cis-reticulatacin

Total synthesis and stereochemical assignment of cis-uvariamicin I and cis-reticulatacin
Total synthesis and stereochemical assignment of cis-uvariamicin I and cis-reticulatacin
Diastereoisomeric mixtures of cis-uvariamicin I (15R,16R,19S,20S,36S and 15S,16S,19R,20R,36S) and cis-reticulatacin (17R,18R,21S,22S,36S and 17S,18S,21R,22R,36S) were synthesized to determine the stereochemistry of the natural products isolated from Annona muricata. It was not possible to resolve a mixture of the four synthetic isomers using chiral HPLC, but the mixed isomers could be distinguished using chiral HPLC EIMS with extracted fragment ion analysis. Comparison of synthetic standards with the natural isolate revealed that cis-uvariamicin I and cis-reticulatacin are present in nature as mixtures of threo-cis-threo diastereoisomers. It is suggested that the nomenclature for the natural products is amended as follows: (15R,16R,19S,20S,36S)-cis-uvariamicin I (cis-uvariamicin IA); (15S,16S,19R,20R,36S)-cis-uvariamicin I (cis-uvariamicin IB); (17R,18R,21S,22S,36S)-cis-reticulatacin (cis-reticulatacin A); (17S,18S,21R,22R,36S)-cis-reticulatacin (cis-reticulatacin B).
0022-3263
6924-6928
Abdel Ghani, Sherif B.
9b8b6bd8-47cd-4268-bfb3-4de0677fb896
Chapman, James M.
85c82662-6c64-4e0c-805c-1ef7a6ad5479
Figadère, Bruno
54577539-81aa-4aca-80f6-67393d6c7c31
Herniman, Julie M.
530b1a36-1386-4602-8df7-defa6eb3512b
Langley, G. John
7ac80d61-b91d-4261-ad17-255f94ea21ea
Niemann, Scott
1b580621-9b97-43f2-8f39-6b19777e9f42
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5
Abdel Ghani, Sherif B.
9b8b6bd8-47cd-4268-bfb3-4de0677fb896
Chapman, James M.
85c82662-6c64-4e0c-805c-1ef7a6ad5479
Figadère, Bruno
54577539-81aa-4aca-80f6-67393d6c7c31
Herniman, Julie M.
530b1a36-1386-4602-8df7-defa6eb3512b
Langley, G. John
7ac80d61-b91d-4261-ad17-255f94ea21ea
Niemann, Scott
1b580621-9b97-43f2-8f39-6b19777e9f42
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5

Abdel Ghani, Sherif B., Chapman, James M., Figadère, Bruno, Herniman, Julie M., Langley, G. John, Niemann, Scott and Brown, Richard C.D. (2009) Total synthesis and stereochemical assignment of cis-uvariamicin I and cis-reticulatacin. Journal of Organic Chemistry, 74 (18), 6924-6928. (doi:10.1021/jo9012578).

Record type: Article

Abstract

Diastereoisomeric mixtures of cis-uvariamicin I (15R,16R,19S,20S,36S and 15S,16S,19R,20R,36S) and cis-reticulatacin (17R,18R,21S,22S,36S and 17S,18S,21R,22R,36S) were synthesized to determine the stereochemistry of the natural products isolated from Annona muricata. It was not possible to resolve a mixture of the four synthetic isomers using chiral HPLC, but the mixed isomers could be distinguished using chiral HPLC EIMS with extracted fragment ion analysis. Comparison of synthetic standards with the natural isolate revealed that cis-uvariamicin I and cis-reticulatacin are present in nature as mixtures of threo-cis-threo diastereoisomers. It is suggested that the nomenclature for the natural products is amended as follows: (15R,16R,19S,20S,36S)-cis-uvariamicin I (cis-uvariamicin IA); (15S,16S,19R,20R,36S)-cis-uvariamicin I (cis-uvariamicin IB); (17R,18R,21S,22S,36S)-cis-reticulatacin (cis-reticulatacin A); (17S,18S,21R,22R,36S)-cis-reticulatacin (cis-reticulatacin B).

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Published date: 18 September 2009

Identifiers

Local EPrints ID: 147641
URI: https://eprints.soton.ac.uk/id/eprint/147641
ISSN: 0022-3263
PURE UUID: 8c3d0aca-81ff-484c-98c7-3b183d9d1948
ORCID for Julie M. Herniman: ORCID iD orcid.org/0000-0003-4834-1093
ORCID for G. John Langley: ORCID iD orcid.org/0000-0002-8323-7235
ORCID for Richard C.D. Brown: ORCID iD orcid.org/0000-0003-0156-7087

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Date deposited: 26 Apr 2010 10:11
Last modified: 19 Nov 2019 02:01

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