TY - JOUR
T1 - Synthesis of Karrikinolide Using the Aldol-Type Acetal Addition Reaction
AU - Kirita, Kanade
AU - Hosokawa, Seijiro
N1 - Funding Information:
We are grateful for the financial support from the Sumitomo Foundation and the Tokyo Biochemical Research Foundation. This work was also supported by the Grant-in-Aid for Scientific Research on Innovative Areas “Frontier Research on Chemical Communications” (18H04632). We also thank Shin-Etsu Chemical Co. Ltd. for supplying TBSCl.
Publisher Copyright:
© 2020 American Chemical Society.
PY - 2020/3/6
Y1 - 2020/3/6
N2 - A short step total synthesis of karrikinolide has been achieved. Both α and α′ positions of O-acylated acetol were alkylated by the boron-mediated aldol-type acetal addition reaction. The one-pot sequence including the Arbuzov reaction, intramolecular Horner-Wadsworth-Emmons reaction, acidic hydrolysis of acetals, and pyran formation provided karrikinolide. This procedure was applicable to the gram-scale synthesis of karrikinolide.
AB - A short step total synthesis of karrikinolide has been achieved. Both α and α′ positions of O-acylated acetol were alkylated by the boron-mediated aldol-type acetal addition reaction. The one-pot sequence including the Arbuzov reaction, intramolecular Horner-Wadsworth-Emmons reaction, acidic hydrolysis of acetals, and pyran formation provided karrikinolide. This procedure was applicable to the gram-scale synthesis of karrikinolide.
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U2 - 10.1021/acs.joc.9b03195
DO - 10.1021/acs.joc.9b03195
M3 - Article
C2 - 31975605
AN - SCOPUS:85081885888
SN - 0022-3263
VL - 85
SP - 3936
EP - 3941
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 5
ER -