Total Synthesis of Theopederin D
- 3 September 2008
- journal article
- research article
- Published by Wiley in Angewandte Chemie-International Edition
- Vol. 47 (38), 7317-7320
- https://doi.org/10.1002/anie.200802548
Abstract
The transformation is complete! The total synthesis of theopederin D (see structure), a potent cytotoxin, has been achieved through oxidative cleavage of a carbon–carbon bond. Other key transformations include an acid‐mediated functionalization of a tetrahydrofuranol, a syn‐selective glycal epoxide ring‐opening, and an asymmetric aldehyde/acid chloride condensation.Keywords
This publication has 45 references indexed in Scilit:
- Synthesis of Psymberin Analogues: Probing a Functional Correlation with the Pederin/Mycalamide Family of Natural ProductsOrganic Letters, 2006
- Convergent Total Synthesis of (+)-Mycalamide AThe Journal of Organic Chemistry, 2006
- Synthesis of Pederic Acid and Related Model StudiesHelvetica Chimica Acta, 2004
- Cinchona Alkaloid-Lewis Acid Catalyst Systems for Enantioselective Ketene−Aldehyde CycloadditionsJournal of the American Chemical Society, 2004
- Catalytic Aerobic Generation of Acyliminium Ions through Electron‐Transfer‐Mediated Carbon‐Carbon Bond ActivationAdvanced Synthesis & Catalysis, 2004
- Highly Diastereoselective Synthesis of Pederic Acid DerivativesThe Journal of Organic Chemistry, 1997
- Highly diastereoselective acetal cleavages using novel reagents prepared from organoaluminum and pentafluorophenolJournal of the American Chemical Society, 1993
- Effects of cyclosporin A, FK 506, and mycalamide A on the activation of murine CD4+ T cells by the murine B7 antigenEuropean Journal of Immunology, 1993
- Change of ras-Transformed NRK-Cells Back to Normal Morphology by Mycalamides A and B, Antitumor Agents from a Marine Sponge.CHEMICAL & PHARMACEUTICAL BULLETIN, 1991
- Synthetic applications of cyclic .alpha.-chloro ethers and thioethers. 4. Use of (thio)acetal esters as reagents for the protection of alcohols. Synthesis of 2-tetrahydrothienyl ethersThe Journal of Organic Chemistry, 1978