- Total synthesis of (-)-borrelidin.
Total synthesis of (-)-borrelidin.
Organic letters (2004-05-21)
Tohru Nagamitsu, Daisuke Takano, Takeo Fukuda, Kazuhiko Otoguro, Isao Kuwajima, Yoshihiro Harigaya, Satoshi Omura
PMID15151434
ABSTRACT
The total synthesis of borrelidin has been achieved. The best feature of our synthetic route is SmI(2)-mediated intramolecular Reformatsky-type reaction for macrocyclization after esterification between two segments. The two key segments were synthesized through chelation-controlled carbotitanation, chelation-controlled hydrogenation, stereoselective Reformatsky reaction, and MgBr(2).Et(2)O-mediated chelation-controlled allylation. [reaction: see text]
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