Synthesis of taurospongin A.
Two new routes to the C(1-10) carboxylic acid core of taurospongin A are presented. In the first route, overall asymmetric hydration of a C(2)-C(3) alkene is achieved by Sharpless AD and selective deoxygenation at C(2); in the second route, the C(3) stereogenic center is set by Tietze asymmetric allylation. A short synthesis of the C(1'-25') fatty acid combines with the product from the first route to complete the total synthesis of taurospongin A.
Wu
Boshen
B
Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK.
Mallinger
Aurélie
A
Robertson
Jeremy
J
D000475:Alkenes / Q000737:chemistry*; D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry
D000475:Alkenes; D000480:Alkynes; C464964:taurospongin A