Practical synthesis of aromatic bisabolanes: Synthesis of 1,3,5-bisabolatrien-7-ol, peniciaculin A and B, and hydroxysydonic acid

TETRAHEDRON

卷:92

Article

Yajima, Arata¹  Shirakawa, Izumi²  Shiotani, Nanami³  Ueda, Kazuya³  Murakawa, Hazuki³  Saito, Tatsuo¹  Katsuta, Ryo¹  Ishigami, Ken¹ 

[1] Tokyo Univ Agr, Dept Chem Life Sci & Agr, Setagaya Ku, 1-1-1 Sakuragaoka, Tokyo 1568502, Japan

[2] Tokyo Univ Agr, Grad Sch Agr, Setagaya Ku, 1-1-1 Sakuragaoka, Tokyo 1568502, Japan

[3] Tokyo Univ Agr, Dept Fermentat Sci, Setagaya Ku, 1-1-1 Sakuragaoka, Tokyo 1568502, Japan

关键词: Aromatic bisabolanes;    Sesquiterpene;    Synthesis;    Asymmetric dihydroxylation;   

DOI  :  10.1016/j.tet.2021.132253

来源: Elsevier

【 摘 要 】

The enantioselective synthesis of aromatic bisabolanes, such as 1,3,5-bisabolatrien-7-ol, peniciaculin A and B, and hydroxysydonic acid, has been described. Our methodology for the total synthesis of aromatic bisabolanes involves the stereoselective construction of the C-7 stereogenic center via a Sharpless asymmetric dihydroxylation reaction, followed by a SmI2-mediated Julia olefination. Preliminary results obtained for the odor evaluation of 1,3,5-bisabolatrien-7-ol and the confirmation of the absolute configurations of peniciaculin A and B are also described. (C) 2021 Elsevier Ltd. All rights reserved.

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