TY  - THES
A1  - Kunz, Oliver
T1  - Die Ringschlussmetathese-/elektrozyklische Ringöffnungssequenz : Entwicklung und Anwendung in der Synthese von Z,E-Diencarbonsäuren
Y1  - 2013
CY  - Potsdam
ER  - 
TY  - JOUR
A1  - Schmidt, Bernd
A1  - Kunz, Oliver
T1  - Stereoselective synthesis of dienyl phosphonates via extended tethered ring-closing metathesis
JF  - Organic letters
N2  - 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.
Y1  - 2013
U6  - https://doi.org/10.1021/ol4020078
SN  - 1523-7060
SN  - 1523-7052
VL  - 15
IS  - 17
SP  - 4470
EP  - 4473
PB  - American Chemical Society
CY  - Washington
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  -