Total Synthesis of Borrelidin

The total synthesis of borrelidin has been achieved. The best feature of our synthetic route is macrocyclization at C11−C12 for the construction of an 18-membered ring after esterification between two segments. A detailed examination of the macrocyclization led us to the samarium(II) iodide-mediated...

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Veröffentlicht in:	Journal of organic chemistry 2007-04, Vol.72 (8), p.2744-2756
Hauptverfasser:	Nagamitsu, Tohru, Takano, Daisuke, Marumoto, Kaori, Fukuda, Takeo, Furuya, Kentaro, Otoguro, Kazuhiko, Takeda, Kazuyoshi, Kuwajima, Isao, Harigaya, Yoshihiro, Ōmura, Satoshi
Format:	Artikel
Sprache:	eng
Schlagworte:	Chemistry Cyclization Exact sciences and technology Fatty Alcohols - chemical synthesis Fatty Alcohols - chemistry Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Molecular Structure Organic chemistry Preparations and properties Stereoisomerism
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Beschreibung
Zusammenfassung:	The total synthesis of borrelidin has been achieved. The best feature of our synthetic route is macrocyclization at C11−C12 for the construction of an 18-membered ring after esterification between two segments. A detailed examination of the macrocyclization led us to the samarium(II) iodide-mediated intramolecular Reformatsky-type reaction as the most efficient synthetic approach. The two key segments were synthesized through regioselective methylation, directed hydrogenation, stereoselective Reformatsky-type reaction, and MgBr2·Et2O-mediated chelation-controlled allylation.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo062089i