Total synthesis of (-)-amathaspiramide F.
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).
Sakaguchi
Kazuhiko
K
Graduate School of Science, Department of Material Science, Osaka City University, Sugimoto, Sumiyoshi, Osaka 558-8585, Japan. sakaguch@sci.osaka-cu.ac.jp
Ayabe
Miki
M
Watanabe
Yusuke
Y
Okada
Takuya
T
Kawamura
Kazushige
K
Shiada
Tetsuro
T
Ohfune
Yasufumi
Y
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
D000475:Alkenes; D011759:Pyrrolidines; D012821:Silanes; D013141:Spiro Compounds; C471225:amathaspiramide F