Pericyclic reactions of prenylated naphthoquinones: Biomimetic syntheses of rubicordifolin and microphyllaquinone

ORGN 701

Jean-Philip Lumb, jplumb@berkeley.edu and Dirk Trauner, trauner@berkeley.edu. Department of Chemistry, University of California, Berkeley, 610 Latimer Hall, Berkeley, CA 94720
Natural products derived from prenylated naphthoquinones have long been recognized for their significant biological activities. In fact, plants that produce compounds of this class are widely used throughout traditional medicine for their therapeutic benefits.  The synthesis of two structurally unique naphthoquinone dimers, rubicordifolin and microphyllaquinone, isolated from Rubia cordifolia and Lippia microphylla respectively, will be discussed.  The biomimetic syntheses highlight reaction cascades that involve pronounced architectural rearrangements with minimal synthetic manipulation.

 

Total Synthesis of Complex Molecules
1:00 PM-5:00 PM, Wednesday, 13 September 2006 Moscone Center -- Room 132, Oral

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006