Total syntheses of (±)-taiwaniaquinol D and (±)-taiwaniaquinone D via a key Lewis acid-catalyzed Nazarov type cyclization. Issue 29 (20th July 2016)

• Record Type: Journal Article
• Authors: Kakde, Badrinath N.; Parida, Amarchand; Kumari, Pooja; Bisai, Alakesh
• Is Part Of: Tetrahedron letters. Volume 57:Issue 29(2016)
• Page Start: 3179
• Page End: 3184
• Publication Date: 2016-07-20
• Subjects: abeo-Abietane -- Total synthesis -- Nazarov cyclization -- Quaternary stereocenter -- Taiwaniaquinoids; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.06.030
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Synthesis of taiwaniaquinoids via a key Nazarov type cyclization has been developed. Only 2 mol % of Bi(OTf)3 is sufficient to construct [6, 5, 6]-core of the natural products. Concise total syntheses of (±)-taiwaniaquinol D and (±)-taiwaniaquinone D are reported. Abstract: Total syntheses of structurally intriguing taiwaniaquinoids viz (±)-taiwaniaquinol D (1e ) and (±)-taiwaniaquinone D (1h ) have been disclosed via a key Lewis acid catalyzed Nazarov type cyclization of arylvinylcarbinols.