Practical synthesis of aromatic bisabolanes: Synthesis of 1, 3, 5-bisabolatrien-7-ol, peniciaculin A and B, and hydroxysydonic acid. (16th July 2021)

• Record Type: Journal Article
• Authors: Yajima, Arata; Shirakawa, Izumi; Shiotani, Nanami; Ueda, Kazuya; Murakawa, Hazuki; Saito, Tatsuo; Katsuta, Ryo; Ishigami, Ken
• Is Part Of: Tetrahedron. Volume 92(2021)
• Publication Date: 2021-07-16
• Subjects: Aromatic bisabolanes -- Sesquiterpene -- Synthesis -- Asymmetric dihydroxylation; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2021.132253
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: 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. Graphical abstract: Image 1