The formal total synthesis of (+)-didemniserinolipid B, a marine tunicate possessing a 6,8-dioxabicyclo[3.2.1]octane framework, was accomplished starting from L-(+)-tartaric acid. The key transformations in the synthesis include the elaboration of a gamma-hydroxy-amide readily obtained by desymmetrization of tartaric acid bis-amide via the controlled addition of a Grignard reagent followed by stereoselective reduction of the resulting ketone. (C) 2010 Elsevier Ltd. All rights reserved.
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Chiba Univ, Grad Sch Pharmaceut Sci, Lab Biofunct Mol Chem, Chuo Ku, 1-8-1 Inohana, Chiba 2608675, JapanChiba Univ, Grad Sch Pharmaceut Sci, Lab Biofunct Mol Chem, Chuo Ku, 1-8-1 Inohana, Chiba 2608675, Japan
Sato, Keigo
Takanashi, Noriyuki
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Chiba Univ, Grad Sch Pharmaceut Sci, Lab Biofunct Mol Chem, Chuo Ku, 1-8-1 Inohana, Chiba 2608675, JapanChiba Univ, Grad Sch Pharmaceut Sci, Lab Biofunct Mol Chem, Chuo Ku, 1-8-1 Inohana, Chiba 2608675, Japan
Takanashi, Noriyuki
Kogure, Noriyuki
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Chiba Univ, Grad Sch Pharmaceut Sci, Lab Biofunct Mol Chem, Chuo Ku, 1-8-1 Inohana, Chiba 2608675, JapanChiba Univ, Grad Sch Pharmaceut Sci, Lab Biofunct Mol Chem, Chuo Ku, 1-8-1 Inohana, Chiba 2608675, Japan
Kogure, Noriyuki
Kitajima, Mariko
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Chiba Univ, Grad Sch Pharmaceut Sci, Lab Biofunct Mol Chem, Chuo Ku, 1-8-1 Inohana, Chiba 2608675, JapanChiba Univ, Grad Sch Pharmaceut Sci, Lab Biofunct Mol Chem, Chuo Ku, 1-8-1 Inohana, Chiba 2608675, Japan
Kitajima, Mariko
Takayama, Hiromitsu
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Chiba Univ, Grad Sch Pharmaceut Sci, Lab Biofunct Mol Chem, Chuo Ku, 1-8-1 Inohana, Chiba 2608675, JapanChiba Univ, Grad Sch Pharmaceut Sci, Lab Biofunct Mol Chem, Chuo Ku, 1-8-1 Inohana, Chiba 2608675, Japan