Unknown

Dataset Information

0

A Relay Strategy Actuates Pre-Existing Trisubstituted Olefins in Monoterpenoids for Cross-Metathesis with Trisubstituted Alkenes.


ABSTRACT: 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).

SUBMITTER: Bahou KA 

PROVIDER: S-EPMC7145354 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature

altmetric image

Publications

A Relay Strategy Actuates Pre-Existing Trisubstituted Olefins in Monoterpenoids for Cross-Metathesis with Trisubstituted Alkenes.

Bahou Karim A KA   Braddock D Christopher DC   Meyer Adam G AG   Savage G Paul GP   Shi Zhensheng Z   He Tianyou T  

The Journal of organic chemistry 20200319 7


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 tris  ...[more]

Similar Datasets

| S-EPMC5967255 | biostudies-literature
| S-EPMC2765515 | biostudies-literature
| S-EPMC4168886 | biostudies-other
| S-EPMC5395252 | biostudies-literature
| S-EPMC2846594 | biostudies-literature
| S-EPMC8232059 | biostudies-literature
| S-EPMC2788204 | biostudies-literature
| S-EPMC7479597 | biostudies-literature
| S-EPMC4978530 | biostudies-literature
| S-EPMC5746592 | biostudies-literature