Revision of the Structure and Total Synthesis of Altenuisol
A total synthesis of the reported structure of altenuisol is described. Comparison of the 1H NMR spectra of the synthesized compound and of the natural product revealed that the originally proposed structure was not correct. Consequently, two constitutional isomers were synthesized. The spectra of o...
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Published in | European journal of organic chemistry Vol. 2012; no. 20; pp. 3863 - 3870 |
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Main Authors | , , |
Format | Journal Article |
Language | English |
Published |
Weinheim
WILEY-VCH Verlag
01.07.2012
WILEY‐VCH Verlag Wiley Wiley-VCH |
Subjects | |
Online Access | Get full text |
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Summary: | A total synthesis of the reported structure of altenuisol is described. Comparison of the 1H NMR spectra of the synthesized compound and of the natural product revealed that the originally proposed structure was not correct. Consequently, two constitutional isomers were synthesized. The spectra of one of these compounds – a structure originally proposed as the structure of altertenuol – matched perfectly with the spectra of the natural product. The total synthesis of altenuisol was thus achieved starting with phloroglucinic acid and protocatechuic aldehyde in 10 steps and in 23 % yield, where the longest linear sequence consisted of 6 steps. The key step was a Suzuki coupling with concomitant formation of the lactone ring. Whether altertenuol is identical with altenuisol could not be decided.
Total synthesis of altenuisol, a minor toxin in ubiquitous Alternaria spp. revealed that the originally proposed structure was not correct. Altenuisol was proved to have an isomeric structure by total synthesis. |
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Bibliography: | ark:/67375/WNG-P2PQK6SW-K Karlsruhe House of Young Scientists (KHYS) istex:9619D500E20814280F9D1C3FD327818451415032 ArticleID:EJOC201200506 Landesgraduiertenförderung Baden-Württemberg |
ISSN: | 1434-193X 1099-0690 |
DOI: | 10.1002/ejoc.201200506 |