title: Total synthesis of (-)-amathaspiramide F.
abstract: The stereoselective total synthesis of the marine alkaloid (-)-amathaspiramide F (1) was achieved from the alpha-hydoxy-alpha-ethynylsilane 2. The crucial steps in this synthesis involved not only the enolate Claisen rearrangement of the alpha-acyloxy-alpha-alkenylsilane 6 for the construction of the nitrogen-containing quaternary carbon center, but also the chemoselective formation of the azaspirohemiaminal 12 using heptamethyldisilazane as the methylamine equivalent and the regioselective dibromination of the phenol moiety of 12 using n-Bu(4)NBrCl(2).
authors.affiliation: Graduate School of Science, Department of Material Science, Osaka City University, Sugimoto, Sumiyoshi, Osaka 558-8585, Japan. sakaguch@sci.osaka-cu.ac.jp
authors.forename: Kazuhiko
authors.initials: K
authors.lastname: Sakaguchi
authors.forename: Miki
authors.initials: M
authors.lastname: Ayabe
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Watanabe
authors.forename: Takuya
authors.initials: T
authors.lastname: Okada
authors.forename: Kazushige
authors.initials: K
authors.lastname: Kawamura
authors.forename: Tetsuro
authors.initials: T
authors.lastname: Shiada
authors.forename: Yasufumi
authors.initials: Y
authors.lastname: Ohfune
mesh_terms: D000475:Alkenes / Q000737:chemistry; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D012821:Silanes / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D011759:Pyrrolidines; D012821:Silanes; D013141:Spiro Compounds; C471225:amathaspiramide F