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Total Synthesis of (−)-Borrelidin

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journal contribution
posted on 27.05.2004 by Tohru Nagamitsu, Daisuke Takano, Takeo Fukuda, Kazuhiko Otoguro, Isao Kuwajima, Yoshihiro Harigaya, Satoshi Ōmura
The total synthesis of borrelidin has been achieved. The best feature of our synthetic route is SmI2-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 MgBr2·Et2O-mediated chelation-controlled allylation.