title: Enantioselective Synthesis of (-)-Acetylapoaranotin.
abstract: The first enantioselective total synthesis of the epipolythiodiketopiperazine (ETP) natural product (-)-acetylapoaranotin (3) is reported. The concise synthesis was enabled by an eight-step synthesis of a key cyclohexadienol-containing amino ester building block. The absolute stereochemistry of both amino ester building blocks used in the synthesis is set through catalytic asymmetric (1,3)-dipolar cycloaddition reactions. The formal syntheses of (-)-emethallicin E and (-)-haemotocin are also achieved through the preparation of a symmetric cyclohexadienol-containing diketopiperazine.
authors.affiliation: The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology , Pasadena, California 91125, United States.
authors.forename: Haoxuan
authors.initials: H
authors.lastname: Wang
authors.affiliation: The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology , Pasadena, California 91125, United States.
authors.forename: Clinton J
authors.initials: CJ
authors.lastname: Regan
authors.affiliation: The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology , Pasadena, California 91125, United States.
authors.forename: Julian A
authors.initials: JA
authors.lastname: Codelli
authors.affiliation: The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology , Pasadena, California 91125, United States.
authors.forename: Paola
authors.initials: P
authors.lastname: Romanato
authors.affiliation: The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology , Pasadena, California 91125, United States.
authors.forename: Angela L A
authors.initials: AL
authors.lastname: Puchlopek-Dermenci
authors.affiliation: The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology , Pasadena, California 91125, United States.
authors.forename: Sarah E
authors.identifier: 0000-0001-8244-9300
authors.initials: SE
authors.lastname: Reisman
mesh_terms: D061565:Cycloaddition Reaction; D054659:Diketopiperazines / Q000737:chemistry*; D004220:Disulfides / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D054659:Diketopiperazines; D004220:Disulfides; C558010:acetylapoaranotin