Abstract
(Matrix presented) Following protection, keto alcohols 4 [from (+)-isomenthone] undergo reduction to 1,3-diol 6 (S configuration at the new stereocenter). Organometallic C-nucleophiles add to the carbonyl with the same facial selectivity as hydride, providing multifunctional derivatives, e.g., 8 and 9, with five contiguous stereocenters. The side chain hydroxyl of 4 is elaborated into amino and amide derivatives (e.g., 12). Structural analysis shows that 6, 8, 9, and the precursor to 12 (10) all adopt triaxial solid-state conformations.
Original language | English |
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Pages (from-to) | 467-470 |
Number of pages | 3 |
Journal | Organic Letters |
Volume | 5 |
Issue number | 4 |
DOIs | |
Publication status | Published - 20 Feb 2003 |
Keywords
- Molecular structure (of isopropylmethylcyclohexanol deriv.); Conformation (prepn., stereostructure, and conformations of bi- and trifunctional (+)-isomenthone derivs.)
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CCDC 208335: Experimental Crystal Structure Determination
Gardiner, J. (Contributor), Crewe, P. D. (Contributor), Smith, G. E. (Contributor), Veal, K. T. (Contributor), Pritchard, R. (Contributor) & Warren, J. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2003
DOI: 10.5517/cc6zshf, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc6zshf&sid=DataCite
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