TY - JOUR
T1 - 2価のパラジウム触媒を用いるエーテル環の立体選択的構築とポリエーテル系天然物Yessotoxin合成への応用
AU - Yokoyama, Hajime
AU - Miyazawa, Masahiro
N1 - Publisher Copyright:
© 2020 Society of Synthetic Organic Chemistry. All rights reserved.
PY - 2020
Y1 - 2020
N2 - The polycyclic ether marine toxin "yessotoxin" was isolated from the digestive glands of the scallop Patinopecten yessoensis, which shows diarrhetic shellfish poisoning. This toxin is produced by dinoflagellates, and consisted of the unique structures, which involves the ladder-shaped and trans-fused polycyclic ethers. Thus several groups have been reported the synthetic studies of this toxin. In recent years, we have been studying the Pd (II)-catalyzed cyclization and its application to the synthesis of natural products, especially aza sugars and alkaloids. Herein we describe the Pd (II)-catalyzed cyclization to ether and its application to the synthetic studies of yessotoxin. This reviews the activation of the allyl alcohol and the stereoselective construction of cyclic ethers by using Pd (II) catalyst. We attained the AB, CD and JK ring systems of yessotoxin, respectively. And the medium-size ether construction is also involved.
AB - The polycyclic ether marine toxin "yessotoxin" was isolated from the digestive glands of the scallop Patinopecten yessoensis, which shows diarrhetic shellfish poisoning. This toxin is produced by dinoflagellates, and consisted of the unique structures, which involves the ladder-shaped and trans-fused polycyclic ethers. Thus several groups have been reported the synthetic studies of this toxin. In recent years, we have been studying the Pd (II)-catalyzed cyclization and its application to the synthesis of natural products, especially aza sugars and alkaloids. Herein we describe the Pd (II)-catalyzed cyclization to ether and its application to the synthetic studies of yessotoxin. This reviews the activation of the allyl alcohol and the stereoselective construction of cyclic ethers by using Pd (II) catalyst. We attained the AB, CD and JK ring systems of yessotoxin, respectively. And the medium-size ether construction is also involved.
KW - Palladium (II) catalyst
KW - Stereoselective cyclization
KW - Tetrahydropyrans
KW - Trans-fused polycyclic ethers
KW - Yessotoxin
UR - http://www.scopus.com/inward/record.url?scp=85084336718&partnerID=8YFLogxK
U2 - 10.5059/yukigoseikyokaishi.78.317
DO - 10.5059/yukigoseikyokaishi.78.317
M3 - 総説
AN - SCOPUS:85084336718
SN - 0037-9980
VL - 78
SP - 317
EP - 326
JO - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
JF - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
IS - 4
ER -