2014
DOI: 10.1002/anie.201410134
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Total Synthesis of Leucosceptroids A and B

Abstract: Leucosceptroids A and B are sesterterpenoids with potent antifeedant and antifungal activities. A more efficient gram-scale total synthesis of leucosceptroid B and the first total synthesis of leucosceptroid A are presented. The key transformations include an aldol reaction between a substituted dihydrofuranone and an (S)-citronellal-derived aldehyde, a SmI2-mediated intramolecular ketyl-olefin radical cyclization, and final-stage alcohol oxidation.

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Cited by 42 publications
(25 citation statements)
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“…39 This carbomagnesiation procedure was applied by the Ma group for an alkyne methylation to obtain intermediate 111 for the total synthesis of leucosceptroids A and B (Scheme 12, f). 40…”
Section: Short Review Syn Thesismentioning
confidence: 99%
“…39 This carbomagnesiation procedure was applied by the Ma group for an alkyne methylation to obtain intermediate 111 for the total synthesis of leucosceptroids A and B (Scheme 12, f). 40…”
Section: Short Review Syn Thesismentioning
confidence: 99%
“…Ma et al described the total syntheses of leucosceptroids A ( 139 ) and B ( 138 ) by applying a SmI 2 -mediated intramolecular ketyl-olefin radical cyclization ( Scheme 21 ) [ 82 ]. These two sesterterpenoids were separated from glandilar trichomes of Leucosceptrum canum [ 83 ].…”
Section: Radical Cyclizationsmentioning
confidence: 99%
“…N-(phenylselenyl)phtalimide was used for the synthesis of the 11-epi-mandelalide A, by the group of Fürstner, 55 while phenylselenylchloride was used by the group of Ma for the synthesis of Leucosceptroids A M A N U S C R I P T A C C E P T E D ACCEPTED MANUSCRIPT and B. 56 One recent example of a synthesis using mercuroetherification was also achieved by Mohapatra and co-workers, using mercury (II) acetate. 57 …”
Section: Scheme 17 : Unexpected Cyclization Toward the Synthesis Of Lmentioning
confidence: 99%