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
T2  - 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
UR  - https://publishup.uni-potsdam.de/frontdoor/index/index/docId/34580
SN  - 1860-5397
VL  - 9
SP  - 2544
EP  - 2555
PB  - Beilstein-Institut zur Förderung der Chemischen Wissenschaften
CY  - Frankfurt, Main
ER  -