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Synfacts 2011(10): 1043-1043
DOI: 10.1055/s-0030-1261146
DOI: 10.1055/s-0030-1261146
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of (+)-Omphadiol
G. Liu, D. Romo*
Texas A&M University, College Station, USA
Further Information
Publication History
Publication Date:
20 September 2011 (online)
Significance
(+)-Omphadiol is a member of the africanane family of sesquiterpenes, isolated from the basidiomycete omphalotus illudens and the edible fungus clavicorona pyxidata. This family contains a 5-7-3 tricyclic core with (+)-omphadiol itself containing six contiguous stereocenters making it a particularly synthetically challenging target. This first total synthesis was completed using an aldol lactonization, a tandem isomerization/ring-closing metathesis and a Simmons-Smith cyclopropanation, giving an overall yield of 16% over ten steps without the use of protecting groups.