title: Total synthesis of the marine alkaloid (-)-lepadin B.
abstract: An enantioselective total synthesis of (-)-lepadin B has been developed starting from (2S,4S)-2,4-O-benzylidene-2, 4-dihydroxybutanal. The key steps in the synthesis include the use of an aqueous intramolecular acylnitroso Diels-Alder reaction to afford the trans-1,2-oxazinolactam and Suzuki cross-coupling reaction to elaborate the (E,E)-octadienyl unit.
authors.affiliation: School of Pharmacy, Tokyo University of Pharmacy & Life Science, Horinouchi, Hachioji, Tokyo 192-0392, Japan.
authors.forename: T
authors.initials: T
authors.lastname: Ozawa
authors.forename: S
authors.initials: S
authors.lastname: Aoyagi
authors.forename: C
authors.initials: C
authors.lastname: Kibayashi
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D000818:Animals; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis*; D010986:Platyhelminths / Q000737:chemistry / Q000378:metabolism; D011804:Quinolines; D013237:Stereoisomerism; D014561:Urochordata / Q000737:chemistry / Q000378:metabolism
chemical_list: D000470:Alkaloids; D006574:Heterocyclic Compounds, 2-Ring; D011804:Quinolines; C414923:lepadin B