Total Synthesis of Neoaltenuene
The total synthesis of neoaltenuene, a toxin produced by alternaria fungi, has been achieved for the first time in 14 steps in a yield of 10 % starting from quinic acid and phloroglucinic acid, the longest linear sequence consisting of 10 steps. The key reaction was a palladium‐catalyzed Suzuki‐type...
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Published in | European Journal of Organic Chemistry Vol. 2009; no. 14; pp. 2275 - 2282 |
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Main Authors | , |
Format | Book Review Journal Article |
Language | English |
Published |
Weinheim
WILEY‐VCH Verlag
01.05.2009
Wiley Wiley-VCH |
Subjects | |
Online Access | Get full text |
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Summary: | The total synthesis of neoaltenuene, a toxin produced by alternaria fungi, has been achieved for the first time in 14 steps in a yield of 10 % starting from quinic acid and phloroglucinic acid, the longest linear sequence consisting of 10 steps. The key reaction was a palladium‐catalyzed Suzuki‐type coupling of an arene boronate with an iodinated cyclohexene.4a‐epi‐Neoaltenuene, a non‐natural isomer has been synthesized similarly. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
The total synthesis of Alternaria metabolite neoaltenuene has been achieved for the first time in 14 steps in a yield of 10 % starting from quinic acid and phloroglucinic acid. The key reactions are a palladium‐catalyzed Suzuki‐type coupling and apalladium(II)‐catalyzed [3,3]‐sigmatropic rearrangement. |
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Bibliography: | Dedicated to Professor Dr. János Rétey on the occasion of his 75th birthday |
ISSN: | 1434-193X 1099-0690 |
DOI: | 10.1002/ejoc.200900125 |