TY - JOUR
T1 - Improved total synthesis of (±)-Tetragocarbone A
AU - Nishimura, Eiji
AU - Yasuno, Yoko
AU - Shinada, Tetsuro
N1 - Funding Information:
We thank the JSPS KAKENHI (No. 15K12758 and 17H05448 ), the Osaka City University Strategic Research Grant for Young Researchers (2016 & 2017), and JGC-S Scholarship Foundation Research Grant for financial support.
Funding Information:
We thank the JSPS KAKENHI (No. 15K12758 and 17H05448), the Osaka City University Strategic Research Grant for Young Researchers (2016 & 2017), and JGC-S Scholarship Foundation Research Grant for financial support.
Publisher Copyright:
© 2018 Elsevier Ltd
PY - 2018/5/24
Y1 - 2018/5/24
N2 - Stereoselective total synthesis of (±)-tetragocarbone A isolated from the propolis of an Australian stingless bee, Tetragonula carbonaria, has been developed by focusing on the latent symmetry of 1. The requisite 1R*, 3R*, 6S* stereogenic centers were selectively installed by hydroxy group directing reactions including the late stage desymmetrization of the 1,3-diketone. The target natural product was successfully prepared in 12 steps from phloroglucinol on 300 mg.
AB - Stereoselective total synthesis of (±)-tetragocarbone A isolated from the propolis of an Australian stingless bee, Tetragonula carbonaria, has been developed by focusing on the latent symmetry of 1. The requisite 1R*, 3R*, 6S* stereogenic centers were selectively installed by hydroxy group directing reactions including the late stage desymmetrization of the 1,3-diketone. The target natural product was successfully prepared in 12 steps from phloroglucinol on 300 mg.
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U2 - 10.1016/j.tet.2018.04.024
DO - 10.1016/j.tet.2018.04.024
M3 - Article
AN - SCOPUS:85045546420
SN - 0040-4020
VL - 74
SP - 2664
EP - 2668
JO - Tetrahedron
JF - Tetrahedron
IS - 21
ER -