Synthetic studies directed toward amphidinol 2: elucidation of the relative configuration of the C1–C10 fragment

Authors

Praveen Kommana
Seung Won Chung
William Donaldson, Marquette UniversityFollow

Document Type

Article

Publication Date

10-2008

Publisher

Elsevier

Source Publication

Tetrahedron Letters

Source ISSN

0040-4039

Abstract

Model compounds (11 and 12) for the C1–C10 tetrahydropyran fragment of amphidinol 2 were prepared from (2S)-benzyloxypropanal in 9 steps. The synthetic route relied on diastereoselective diene-aldehyde cycloaddition, stereoselective C-allylation, and reagent based enantioselective aldehyde allylation. Comparison of the NMR spectra for models 11 and 12 with that for amphidinol 2 indicated that the C1–C10 segment of the natural product possesses the 2R^*,4R^*,6R^*,7S^*,8R^*,10S^* relative configuration.

Comments

Accepted version. Tetrahedron Letters, Volume 49, Issue 43 (October 2008) pp. 6209-6211. DOI: 10.1016/j.tetlet.2008.08.035. © 2008 Elsevier. Used with permission.

Recommended Citation

Kommana, Praveen; Chung, Seung Won; and Donaldson, William, "Synthetic studies directed toward amphidinol 2: elucidation of the relative configuration of the C1–C10 fragment" (2008). Chemistry Faculty Research and Publications. 47.
https://epublications.marquette.edu/chem_fac/47