Computational structure revision of a longipinane derivative meridane. Issue 42 (19th October 2016)

• Record Type: Journal Article
• Authors: Reddy, D. Sai; Kutateladze, Andrei G.
• Is Part Of: Tetrahedron letters. Volume 57:Issue 42(2016)
• Page Start: 4727
• Page End: 4729
• Publication Date: 2016-10-19
• Subjects: Longipinanes -- Meridane -- Structure revision -- Relativistic force field (DU8c) -- Nuclear spin–spin coupling constants; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.09.030
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Misassigned structure of a sesquiterpene meridane is computationally corrected. Besides chemical shifts, J H–H and J C–H are computed with rff to aid in revision. Structure correction necessitated revision of the mechanism of meridane's formation. Abstract: Structure revision of a recently reported longipinane derivative, meridane, was enabled by computations of its NMR spectra. This structural revision necessitates corrections in the originally proposed Wagner–Meerwein mechanism for the formation of meridane.