Towards the total synthesis of 9, 11-secosterol: Linking A, B- and D-rings with Michael addition to sulfone-activated cyclopentenone. (25th April 2023)

• Record Type: Journal Article
• Authors: Kõllo, Marek; Rõuk, Kristi; Järving, Ivar; Pehk, Tõnis; Lopp, Margus
• Is Part Of: Tetrahedron. Volume 136(2023)
• Publication Date: 2023-04-25
• Subjects: Michael addition -- Sulfones -- 9, 11-Secosterols -- Total synthesis -- Relative configuration; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2023.133363
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: The application of Michael addition to the construction of the carbon skeleton of 9, 11-secosterols has been investigated using the following Michael acceptor - sulfone 2-[(4-methylphenyl)sulfonyl]cyclopent-2-en-1-one, where the addition product was isolated in good yield and as a mixture of two diastereomers. Also, the diastereomers were separable by crystallization, and, based on NMR spectroscopic data, the relative configuration of the formed stereocentres of the isolated diastereomer matched the 9, 11-secosterol found in nature. This study can be exploited to create a total synthesis scheme for 9, 11-secosterols. Graphical abstract: Image 1