Correlation Engine 2.0
Clear Search sequence regions

Sizes of these terms reflect their relevance to your search.

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).


Kazuhiko Sakaguchi, Miki Ayabe, Yusuke Watanabe, Takuya Okada, Kazushige Kawamura, Tetsuro Shiada, Yasufumi Ohfune. Total synthesis of (-)-amathaspiramide F. Organic letters. 2008 Dec 4;10(23):5449-52

Expand section icon Mesh Tags

Expand section icon Substances

PMID: 18973331

View Full Text