title: A Biomimetic Synthesis of Phaitanthrin E Involving a Fragmentation of sp(3) Carbon-Carbon Bond: Synthesis and Rearrangement of Phaitanthrin D to Phaitanthrin E.
abstract: A biogenetic type total synthesis of alkaloids phaitanthrin D and phaitanthrin E has been described. The Csp(3)-Csp(3) bond cleavage with the release of several heteroatoms bearing unexpected leaving groups in intramolecular substitution reactions on an iminium double bond in the quinazolinones has been demonstrated using HMDS/ZnCl2 or NaHMDS. The mechanistic aspects have been supported by isolation and characterization of appropriate intermediates.
authors.affiliation: Division of Organic Chemistry, National Chemical Laboratory (CSIR) , Pune 411 008, India.
authors.forename: Sagar D
authors.initials: SD
authors.lastname: Vaidya
authors.affiliation: Division of Organic Chemistry, National Chemical Laboratory (CSIR) , Pune 411 008, India.
authors.forename: Narshinha P
authors.initials: NP
authors.lastname: Argade
mesh_terms: D000470:Alkaloids / Q000737:chemistry; D032701:Biomimetics; D015394:Molecular Structure; D029595:Orchidaceae / Q000737:chemistry; D052999:Quinazolinones / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D052999:Quinazolinones; C000607089:phaitanthrin D; C000607090:phaitanthrin E