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

Karim A. Bahou | Zendy; D. Christopher Braddock | Zendy; Adam G. Meyer | Zendy; G. Paul Savage | Zendy; Zhensheng Shi | Zendy; Tianyou He | Zendy

Open Access

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

Author(s) -

Karim A. Bahou,

D. Christopher Braddock,

Adam G. Meyer,

G. Paul Savage,

Zhensheng Shi,

Tianyou He

Publication year - 2020

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.0c00067

Subject(s) - chemistry , retrosynthetic analysis , olefin metathesis , metathesis , olefin fiber , ruthenium , combinatorial chemistry , organic chemistry , catalysis , total synthesis , polymerization , polymer

A retrosynthetic disconnection-reconnection analysis of epoxypolyenes-substrates that can undergo cyclization to podocarpane-type tricycles-reveals relay-actuated Δ 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 Δ 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).

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