@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}
}

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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  - 

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