title: Total synthesis of diaporthichalasin by using the intramolecular Diels-Alder reaction of an α,β-unsaturated γ-hydroxylactam in aqueous media.
abstract: The first total synthesis of diaporthichalasin has been successfully achieved and complete structure elucidation, including the absolute configuration, was also accomplished. The intramolecular Diels-Alder (IMDA) reaction between the diene side chain on the decalin skeleton and α,β-unsaturated γ-hydroxy-γ-lactam in aqueous media was effectively employed as the key step. From this synthetic study, we found that α,β-unsaturated γ-hydroxy-γ-lactam is an essential precursor for the construction of the diaporthichalasin-type pentacyclic skeleton. This important finding strongly suggests that this route is involved in the biosynthetic pathway for diaporthichalasin.
authors.affiliation: Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba 278-8510, Japan.
authors.forename: Nobuhiro
authors.initials: N
authors.lastname: Shionozaki
authors.forename: Naoki
authors.initials: N
authors.lastname: Iwamura
authors.forename: Ryo
authors.initials: R
authors.lastname: Tanaka
authors.forename: Kimiko
authors.initials: K
authors.lastname: Makino
authors.forename: Hiromi
authors.initials: H
authors.lastname: Uchiro
mesh_terms: D003500:Cyclization; D061565:Cycloaddition Reaction; D003572:Cytochalasins / Q000138:chemical synthesis* / Q000737:chemistry; D007769:Lactams / Q000737:chemistry*; D015394:Molecular Structure; D014867:Water / Q000737:chemistry*
chemical_list: D003572:Cytochalasins; D007769:Lactams; C575781:diaporthichalasin; D014867:Water