2020
DOI: 10.1002/anie.202008158
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Total Synthesis of (+)‐Cornexistin

Abstract: Herein, we describe the first total synthesis of (+)‐cornexistin as well as its 8‐epi‐isomer starting from malic acid. The robust and scalable route features a Nozaki–Hiyama–Kishi reaction, an auxiliary‐controlled syn‐Evans‐aldol reaction, and a highly efficient intramolecular alkylation to form the nine‐membered carbocycle. The delicate maleic anhydride moiety of the nonadride skeleton was constructed from a β‐keto nitrile. The developed route enabled the synthesis of 165 mg (+)‐cornexistin.

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Cited by 15 publications
(12 citation statements)
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“…However, these approaches eventually had to be abandoned due to a lack of scalability. Alternatively, forging the bond between C5 and C6 via intramolecular allylic alkylation turned out to be highly scalable and delivered the nine‐membered carbocycle in good yields [12] …”
Section: Resultsmentioning
confidence: 99%
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“…However, these approaches eventually had to be abandoned due to a lack of scalability. Alternatively, forging the bond between C5 and C6 via intramolecular allylic alkylation turned out to be highly scalable and delivered the nine‐membered carbocycle in good yields [12] …”
Section: Resultsmentioning
confidence: 99%
“…This observation was in accordance with the results obtained for the attempted formation of the enol triflate employing model substrate 59 . A screen of more than 30 triflation conditions resulted in either recovery of unreacted starting material or decomposition of 59 [12] . Treatment with TfCl also delivered exclusively the α‐chlorinated product.…”
Section: Resultsmentioning
confidence: 99%
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