A General Approach to the Basiliolide/Transtaganolide Natural Products: Total Syntheses of Basiliolide B, epi-8-Basiliolide B, Transtaganolide C, and Transtaganolide D
KAUST Grant NumberKUS-11-006-02
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Abstract(Figure Presented) In a flash: The total synthesis of transtaganolide and basiliolide natural products is achieved in three steps from achiral, monocyclic esters (see scheme). Featured in the syntheses are an Ireland-Claisen/Diels- Alder cascade and a novel methoxyacetylide coupling/cyclization sequence. © 2011 Wiley-VCH Verlag GmbH & Co. KGaA.
CitationNelson HM, Murakami K, Virgil SC, Stoltz BM (2011) A General Approach to the Basiliolide/Transtaganolide Natural Products: Total Syntheses of Basiliolide B, epi-8-Basiliolide B, Transtaganolide C, and Transtaganolide D. Angew Chem Int Ed 50: 3688–3691. Available: http://dx.doi.org/10.1002/anie.201008003.
SponsorsThis publication is based on work supported by Award No. KUS-11-006-02, made by King Abdullah University of Science and Technology (KAUST). The authors wish to thank the NSF and Ford Foundation (predoctoral fellowship to H.M.N.), the Japan Society for the Promotion of Science (fellowship for K. M.), Amgen, Abbott, Boehringer Ingelheim, the Gordon and Betty Moore Foundation, and Caltech for financial support. Dr. J. T. Mohr is gratefully acknowledged for useful discussions. Larry Henling and Dr. Michael Day are acknowledged for X-ray analysis of 1a. The Bruker KAPPA APEXII X-ray diffractometer used in this study was purchased through an NSF CRIF:MU award to Caltech, CHE-0639094.
CollectionsPublications Acknowledging KAUST Support
- The total syntheses of basiliolide C, epi-basiliolide C, and protecting-group-free total syntheses of transtaganolides C and D.
- Authors: Gordon JR, Nelson HM, Virgil SC, Stoltz BM
- Issue date: 2014 Oct 17
- Diastereoselective Total Synthesis of (±)-Basiliolide B and (±)-epi-8-Basiliolide B.
- Authors: Liang X, Zhou L, Min L, Ye W, Bao W, Ma W, Yang Q, Qiao F, Zhang X, Lee CS
- Issue date: 2017 Apr 7
- Total syntheses of (-)-transtaganolide A, (+)-transtaganolide B, (+)-transtaganolide C, and (-)-transtaganolide D and biosynthetic implications.
- Authors: Nelson HM, Gordon JR, Virgil SC, Stoltz BM
- Issue date: 2013 Jun 24
- Base-catalyzed Diels-Alder reactions of 2H-pyran-2,5-diones: a mild approach to basiliolide B.
- Authors: Zhou X, Wu W, Liu X, Lee CS
- Issue date: 2008 Dec 18
- Skeletal and stereochemical diversification of tricyclic frameworks inspired by Ca(2+)-ATPase inhibitors, artemisinin and transtaganolide D.
- Authors: Oguri H, Yamagishi Y, Hiruma T, Oikawa H
- Issue date: 2009 Feb 5