| Title: | "Desymmetrization by ring-closing metathesis leading to 6,8-dioxabicyclo[3.2.1]octanes: a new route for the synthesis of (+)-exo- and endo-brevicomin" |
| Author(s): | Burke SD; Muller N; Beaudry CM; |
| Address: | "Department of Chemistry, University of Wisconsin-Madison 53706-1396, USA. burke@chem.wisc.edu" |
| ISSN/ISBN: | 1523-7060 (Print) 1523-7052 (Linking) |
| Abstract: | "[formula: see text] The 6,8-dioxabicyclo[3.2.1]octane skeleton is a common structural subunit in natural products. A conceptionally new strategy affording these structures is described for the syntheses of (+)-exo-brevicomin and rac-endo- and enantiomerically enriched (+)-endo-brevicomin, employing desymmetrization of trienes derived from diols with C2 and meso symmetry via ring-closing metathesis" |
| Keywords: | "Animals Bridged Bicyclo Compounds, Heterocyclic/*chemical synthesis Catalysis Coleoptera/chemistry Heterocyclic Compounds, 2-Ring/*chemical synthesis Octanes/*chemical synthesis Sex Attractants/*chemical synthesis Stereoisomerism;" |
| Notes: | "MedlineBurke, S D Muller, N Beaudry, C M eng CA74394/CA/NCI NIH HHS/ Research Support, Non-U.S. Gov't Research Support, U.S. Gov't, P.H.S. 2000/06/03 Org Lett. 1999 Dec 2; 1(11):1827-9. doi: 10.1021/ol9910971" |
