In this section
@article{Bahou:2020:10.1021/acs.joc.0c00067,
author = {Bahou, K and Braddock, D and Meyer, A and Savage, P and Shi, Z and He, T},
doi = {10.1021/acs.joc.0c00067},
journal = {The Journal of Organic Chemistry},
pages = {4906--4917},
title = {A relay strategy actuates pre-existing trisubstituted olefins in monoterpenoids for cross metathesis with trisubstituted alkenes},
url = {http://dx.doi.org/10.1021/acs.joc.0c00067},
volume = {85},
year = {2020}
}
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 -