216868-38-1Relevant academic research and scientific papers
Synthesis of the Death-Cap Mushroom Toxin α-Amanitin
Matinkhoo, Kaveh,Pryyma, Alla,Todorovic, Mihajlo,Patrick, Brian O.,Perrin, David M.
supporting information, p. 6513 - 6517 (2018/06/08)
α-Amanitin is an extremely toxic bicyclic octapeptide isolated from the death-cap mushroom, Amanita phalloides. As a potent inhibitor of RNA polymerase II, α-amanitin is toxic to eukaryotic cells. Recent interest in α-amanitin arises from its promise as a payload for antibody-drug conjugates. For over 60 years, A. phalloides has been the only source of α-amanitin. Here we report a synthesis of α-amanitin, which surmounts the key challenges for installing the 6-hydroxy-tryptathionine sulfoxide bridge, enantioselective synthesis of (2S,3R,4R)-4,5-dihydroxy-isoleucine, and diastereoselective sulfoxidation.
Synthesis of a 35-member stereoisomer library of bistramide A: Evaluation of effects on actin state, cell cycle and tumor cell growth
Wrona, Iwona E.,Lowe, Jason T.,Turbyville, Thomas J.,Johnson, Tanya R.,Beignet, Julien,Beutler, John A.,Panek, James S.
supporting information; experimental part, p. 1897 - 1916 (2009/07/01)
Synthesis and preliminary biological evaluation of a 35-member library of bistramide A stereoisomers are reported. All eight stereoisomers of the C1-C13 tetrahydropyran fragment of the molecule were prepared utilizing crotylsilane reagents 9 and 10 in our
An efficient protocol for the stereoselective dihydroxylation of ene- ester systems
Hermitage, Stephen A.,Murphy, Alison,Nielsen, Poul,Roberts, Stanley M.
, p. 13185 - 13202 (2007/10/03)
Dihydroxylation of ene ester systems was achieved in good yield and diastereoselectivity under classical catalytic OsO4 and NMO conditions using the intrinsic diastereoselectivity in α-methyl β-OTBS systems. This intrinsic diastereoselection ca
