@article{SchmidtKunz2013, author = {Schmidt, Bernd and Kunz, Oliver}, title = {Stereoselective synthesis of dienyl phosphonates via extended tethered ring-closing metathesis}, series = {Organic letters}, volume = {15}, journal = {Organic letters}, number = {17}, publisher = {American Chemical Society}, address = {Washington}, issn = {1523-7060}, doi = {10.1021/ol4020078}, pages = {4470 -- 4473}, year = {2013}, abstract = {Allylphosphonates of allylic alcohols were converted to conjugated dienyl phosphonates in a one-flask reaction, comprising a ring-closing metathesis (RCM), a base-induced ring-opening, and an alkylation. The ring-opening proceeds with very high diastereoselectivity, giving exclusively the (1Z,3E)-configured dienes. Single diastereomers and mixtures of diastereomers can be used as starting materials without noticeable effect on the diastereoselectivity of the sequence.}, language = {en} } @article{SchmidtKunz2013, author = {Schmidt, Bernd and Kunz, Oliver}, title = {Bidirectional cross metathesis and ring-closing metathesis/ring opening of a C-2-symmetric building block: a strategy for the synthesis of decanolide natural products}, series = {Beilstein journal of organic chemistry}, volume = {9}, journal = {Beilstein journal of organic chemistry}, publisher = {Beilstein-Institut zur F{\"o}rderung der Chemischen Wissenschaften}, address = {Frankfurt, Main}, issn = {1860-5397}, doi = {10.3762/bjoc.9.289}, pages = {2544 -- 2555}, year = {2013}, abstract = {Starting from the conveniently available ex-chiral pool building block (R,R)-hexa-1,5-diene-3,4-diol, the ten-membered ring lactones stagonolide E and curvulide A were synthesized using a bidirectional olefin-metathesis functionalization of the terminal double bonds. Key steps are (i) a site-selective cross metathesis, (ii) a highly diastereoselective extended tethered RCM to furnish a (Z,E)-configured dienyl carboxylic acid and (iii) a Ru-lipase-catalyzed dynamic kinetic resolution to establish the desired configuration at C9. Ring closure was accomplished by macrolactonization. Curvulide A was synthesized from stagonolide E through Sharpless epoxidation.}, language = {en} } @phdthesis{Kunz2013, author = {Kunz, Oliver}, title = {Die Ringschlussmetathese-/elektrozyklische Ring{\"o}ffnungssequenz : Entwicklung und Anwendung in der Synthese von Z,E-Diencarbons{\"a}uren}, address = {Potsdam}, pages = {193 S.}, year = {2013}, language = {de} }