TY  - JOUR
A1  - Schmidt, Bernd
A1  - Audoersch, Stephan
A1  - Kunz, Oliver
T1  - Stereoselective Synthesis of 2Z,4E-Configured Dienoates through Tethered Ring Closing Metathesis
JF  - Synthesis
KW  - allyl alcohols
KW  - dienes
KW  - ring closing metathesis
KW  - ruthenium
KW  - elimination
Y1  - 2016
U6  - https://doi.org/10.1055/s-0035-1562536
SN  - 0039-7881
SN  - 1437-210X
VL  - 48
SP  - 4509
EP  - 4518
PB  - Thieme
CY  - Stuttgart
ER  - 
TY  - JOUR
A1  - Schmidt, Bernd
A1  - Kunz, Oliver
T1  - 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
JF  - Beilstein journal of organic chemistry
N2  - 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.
KW  - dienes
KW  - enzyme catalysis
KW  - lactones
KW  - metathesis
KW  - natural products
KW  - ruthenium
Y1  - 2013
U6  - https://doi.org/10.3762/bjoc.9.289
SN  - 1860-5397
VL  - 9
SP  - 2544
EP  - 2555
PB  - Beilstein-Institut zur Förderung der Chemischen Wissenschaften
CY  - Frankfurt, Main
ER  - 
TY  - JOUR
A1  - Schmidt, Bernd
A1  - Kunz, Oliver
T1  - alpha,beta-Unsaturated delta-Valerolactones through RCM-Isomerization Sequence
JF  - Synlett : accounts and rapid communications in synthetic organic chemistry
N2  - alpha,beta-Unsaturated d-lactones are accessible via a sequential ring-closing metathesis (RCM) double-bond migration reaction starting from butenoates of allyl alcohols. This approach proceeds efficiently with lower catalyst loadings and higher initial substrate concentrations compared to the alternative RCM of acrylates derived from homoallylic alcohols.
KW  - ruthenium
KW  - lactones
KW  - tandem reactions
KW  - metathesis
KW  - esters
Y1  - 2012
U6  - https://doi.org/10.1055/s-0031-1290488
SN  - 0936-5214
IS  - 6
SP  - 851
EP  - 854
PB  - Thieme
CY  - Stuttgart
ER  -