title: A unified bioinspired "aplysinopsin cascade": total synthesis of (±)-tubastrindole B and related biosynthetic congeners.
abstract: Applying a biomimetic approach, the first total synthesis of (±)-tubastrindole B is reported herein. This work features a ring-expansion cascade of a dictazole-type precursor into cycloaplysinopsin-type congeners. Moreover, the isolation of a transient biogenetic intermediate represents a milestone in the biosynthetic understanding of this family of marine alkaloids.
authors.affiliation: Laboratoire de pharmacognosie, Université Paris-Sud , UMR CNRS 8076 BioCIS, LabEx LERMIT, Faculté de Pharmacie, 5, rue Jean-Baptiste Clément, 92296 Châtenay-Malabry, France.
authors.forename: Adam
authors.initials: A
authors.lastname: Skiredj
authors.forename: Mehdi A
authors.initials: MA
authors.lastname: Beniddir
authors.forename: Delphine
authors.initials: D
authors.lastname: Joseph
authors.forename: Karine
authors.initials: K
authors.lastname: Leblanc
authors.forename: Guillaume
authors.initials: G
authors.lastname: Bernadat
authors.forename: Laurent
authors.initials: L
authors.lastname: Evanno
authors.forename: Erwan
authors.initials: E
authors.lastname: Poupon
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry; D000818:Animals; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D008386:Marine Biology; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism; D014364:Tryptophan / Q000031:analogs & derivatives / Q000737:chemistry
chemical_list: D000470:Alkaloids; D007211:Indoles; C531880:tubastrindole B; C015685:aplysinopsin; D014364:Tryptophan