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Facile and Efficient Synthesis of Lactols by a Domino Reaction of 2,3‐Epoxy Alcohols with a Hypervalent Iodine(III) Reagent and Its Application to the Synthesis of Lactones and the Asymmetric Synthesis of (+)‐Tanikolide
Author(s) -
Fujioka Hiromichi,
Matsuda Satoshi,
Horai Mai,
Fujii Eri,
Morishita Maiko,
Nishiguchi Natsuko,
Hata Kayoko,
Kita Yasuyuki
Publication year - 2007
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200601341
Subject(s) - hypervalent molecule , chemistry , lactol , epoxy , reagent , alcohol , cascade reaction , organic chemistry , alkyl , lactone , domino , formylation , combinatorial chemistry , catalysis
The domino reaction of 2,3‐epoxy‐1‐alcohol derivatives, namely tetrasubstituted 2,3‐epoxy‐1‐alcohols and 2‐ or 3‐alkyl trisubstituted 2,3‐epoxy‐1‐alcohols, with PhI(OCOCF 3 ) 2 in the presence of H 2 O is described in detail. In this reaction, several types of lactol derivatives can be directly obtained from the 2,3‐epoxy‐1‐alcohol derivatives in a single operation. The obtained lactols were successively converted into the corresponding lactones. This reaction is applicable to the construction of optically active lactone compounds. The asymmetric total synthesis of (+)‐tanikolide, an antifungal marine natural product, has been effectively achieved by using this reaction.