Total synthesis of smenochromene B

ORGN 716

Michael Kienzler, mkienzler@berkeley.edu1, Carla P. D. C. P. Rosa2, Brooke Olson3, and Dirk Trauner, trauner@berkeley.edu1. (1) Department of Chemistry, University of California, Berkeley, 613 Latimer Hall, Berkeley, CA 94720, (2) Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, United Kingdom, (3) Theravance Inc
The total synthesis of smenochromene B was achieved through a Lewis acid catalyzed macrocyclization followed by a novel ring contraction with concomitant double bond isomerization. Molecular modeling was used to gain further insight into the rearrangement of smenochromene D to a precursor of smenochromene B.

 

Total Synthesis, Materials, Molecular Recognition, Process R&D, and Physical Organic Chemistry
8:00 PM-10:00 PM, Wednesday, 13 September 2006 Moscone Center -- Hall D, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 11 September 2006 Moscone Center -- Hall D, Sci-Mix

Division of Organic Chemistry

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