Stereoselective Total Synthesis of the Proposed Structure of 2-Epibotcinolide

The total synthesis of pseudo 2-epibotcinolide (1b) through several featured synthetic approaches has been attained. First, the chiral linear precursors of the nine-membered ring compound is stereoselectively constructed by the asymmetric aldol reaction for producing β-hydroxy ester units. Second, t...

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Veröffentlicht in:Organic letters 2006-11, Vol.8 (23), p.5279-5282
Hauptverfasser: Shiina, Isamu, Takasuna, Yu-ji, Suzuki, Ryo-suke, Oshiumi, Hiromi, Komiyama, Yuri, Hitomi, Seiichi, Fukui, Hiroki
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Sprache:eng
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Zusammenfassung:The total synthesis of pseudo 2-epibotcinolide (1b) through several featured synthetic approaches has been attained. First, the chiral linear precursors of the nine-membered ring compound is stereoselectively constructed by the asymmetric aldol reaction for producing β-hydroxy ester units. Second, the key cyclization reaction to form the nine-membered lactone moiety is efficiently achieved by the extremely facile and powerful mixed-anhydride method promoted by 2-methyl-6-nitrobenzoic anhydride (MNBA) with basic promoters.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol062058+