Citation

BibTex format

@article{Bahou:2019:10.26434/chemrxiv.8267837.v3,
author = {Bahou, K and Braddock, DC and Meyer, AG and Savage, GP and Shi, Z and He, T},
doi = {10.26434/chemrxiv.8267837.v3},
title = {A Relay Strategy Actuates Pre-Existing Trisubstituted Olefins in Monoterpenoids to Form New Trisubstituted Olefins by Cross Metathesis},
url = {http://dx.doi.org/10.26434/chemrxiv.8267837.v3},
year = {2019}
}

RIS format (EndNote, RefMan)

TY  - JOUR
AB - <jats:p><jats:bold><jats:underline>Abstract:</jats:underline></jats:bold> A retrosynthetic disconnection-reconnection analysis of epoxypolyenes – substrates that can undergo cyclization to podocarpane-type tricycles – reveals relay-actuated Δ<jats:sup>6,7</jats:sup>-functionalized monoterpenoid alcohols for ruthenium benzylidene catalyzed olefin cross metathesis with homoprenyl benzenes. Successful implementation of this approach provided several epoxypolyenes as expected (<jats:italic>E</jats:italic>:<jats:italic>Z</jats:italic>, ca. 2-3:1). The method is further generalized for the cross metathesis of pre-existing trisubstituted olefins in other relay-actuated Δ<jats:sup>6,7</jats:sup>-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 <jats:italic>E</jats:italic>-geometrical isomer).</jats:p><jats:p />
AU - Bahou,K
AU - Braddock,DC
AU - Meyer,AG
AU - Savage,GP
AU - Shi,Z
AU - He,T
DO - 10.26434/chemrxiv.8267837.v3
PY - 2019///
TI - A Relay Strategy Actuates Pre-Existing Trisubstituted Olefins in Monoterpenoids to Form New Trisubstituted Olefins by Cross Metathesis
UR - http://dx.doi.org/10.26434/chemrxiv.8267837.v3
ER -