TY - JOUR AB - A retrosynthetic disconnection-reconnection analysis of epoxypolyenes – substrates that can undergo cyclization to podocarpane-type tricycles – reveals relay-actuated 6,7-functionalized monoterpenoid alcohols for ruthenium benzylidene catalyzed olefin cross metathesis with homoprenyl benzenes. Successful implementation of this approach provided several epoxypolyenes as expected (E:Z, ca. 2-3:1). The method is further generalized for the cross metathesis of pre-existing trisubstituted olefins in other relay-actuated 6,7-functionalized monoterpenoid alcohols with various other trisubstituted alkenes to form new trisubstituted olefins. Epoxypolyene cyclization of an enantiomerically pure, but geometrically impure, epoxypolyene substrate provides an enantiomerically pure, trans-fused, podocarpane-type tricycle (from the E-geometrical isomer). AU - Bahou,K AU - Braddock,D AU - Meyer,A AU - Savage,P AU - Shi,Z AU - He,T DO - 10.1021/acs.joc.0c00067 EP - 4917 PY - 2020/// SN - 0022-3263 SP - 4906 TI - A relay strategy actuates pre-existing trisubstituted olefins in monoterpenoids for cross metathesis with trisubstituted alkenes T2 - The Journal of Organic Chemistry UR - http://dx.doi.org/10.1021/acs.joc.0c00067 UR - https://pubs.acs.org/doi/abs/10.1021/acs.joc.0c00067 UR - http://hdl.handle.net/10044/1/77166 VL - 85 ER -