Stereoselective total synthesis of the proposed structure of 2-epibotcinolide.
[Structure: see text] 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 beta-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.
Shiina
Isamu
I
Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan. shiina@ch.kagu.tus.ac.jp
Takasuna
Yu-Ji
YJ
Suzuki
Ryo-Suke
RS
Oshiumi
Hiromi
H
Komiyama
Yuri
Y
Hitomi
Seiichi
S
Fukui
Hiroki
H
D020171:Botrytis / Q000378:metabolism; D003500:Cyclization; D003651:Decanoates / Q000138:chemical synthesis* / Q000378:metabolism; D007783:Lactones / Q000138:chemical synthesis* / Q000378:metabolism; D015394:Molecular Structure; D011753:Pyrones / Q000138:chemical synthesis* / Q000378:metabolism
D003651:Decanoates; D007783:Lactones; D011753:Pyrones; C511119:botcinin E