Double bond formation based on nitroaldol reaction and radical elimination: A prototype segment connection method for the total synthesis of nigricanoside A dimethyl ester. Issue 19 (9th May 2018)

• Record Type: Journal Article
• Authors: Tsunoda, Takayuki; Fujiwara, Kenshu; Okamoto, Satoshi; Kondo, Yoshihiko; Akiba, Uichi; Ishigaki, Yusuke; Katoono, Ryo; Suzuki, Takanori
• Is Part Of: Tetrahedron letters. Volume 59:Issue 19(2018)
• Page Start: 1846
• Page End: 1850
• Publication Date: 2018-05-09
• Subjects: Natural product synthesis -- Nitroaldol reaction -- Radical elimination -- Double bond formation -- β-Chloronitroalkane; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.03.091
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A prototype segment connection method for the synthesis of nigricanoside A dimethyl ester. Olefination to give a double bond, which has an ether group at an allylic position. Olefination by nitroaldol reaction, chlorination or thionocarbonylation, and radical elimination. Abstract: During the course of our studies toward the total synthesis of nigricanoside A dimethyl ester, a prototype method for the connection of the left- and right-half segments at the C9′–C10′ double bond was developed using a model system. The method was based on a simple three-step process including: (i) a nitroaldol reaction, (ii) chlorination or thionocarbonylation, and (iii) radical elimination.