@article{Bahou:2019:10.26434/chemrxiv.8267837,
author = {Bahou, K and Braddock, DC and Meyer, AG and Savage, GP and Shi, Z and He, T},
doi = {10.26434/chemrxiv.8267837},
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},
year = {2019}
}

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TY  - JOUR
AB  - <jats:p><b><u>Abstract:</u></b> A retrosynthetic disconnection-reconnection analysis of epoxypolyenes – substrates that can undergo cyclization to podocarpane-type tricycles – reveals relay-actuated Δ<sup>6,7</sup>-functionalized monoterpenoid alcohols for ruthenium benzylidene catalyzed olefin cross metathesis with homoprenyl benzenes. Successful implementation of this approach provided several epoxypolyenes as expected (<i>E</i>:<i>Z</i>, ca. 2-3:1). The method is further generalized for the cross metathesis of pre-existing trisubstituted olefins in other relay-actuated Δ<sup>6,7</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 <i>E</i>-geometrical isomer).<br></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
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
ER  - 

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