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.
[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.
Burke
S D
SD
Department of Chemistry, University of Wisconsin-Madison 53706-1396, USA. burke@chem.wisc.edu
Müller
N
N
Beaudry
C M
CM
D000818:Animals; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D002384:Catalysis; D001517:Coleoptera / Q000737:chemistry; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis*; D009795:Octanes / Q000138:chemical synthesis*; D012724:Sex Attractants / Q000138:chemical synthesis*; D013237:Stereoisomerism
D019086:Bridged Bicyclo Compounds, Heterocyclic; D006574:Heterocyclic Compounds, 2-Ring; D009795:Octanes; D012724:Sex Attractants; C012219:brevicomin