Stereocontrolled radical bicyclizations of oxygenated precursors enable short syntheses of oxidized abietane diterpenoids
D Vrubliauskas, BM Gross… - Journal of the American …, 2021 - ACS Publications
The power of cation-initiated cyclizations of polyenes for the synthesis of polycyclic
terpenoids cannot be overstated. However, a major limitation is the intolerance of many …
terpenoids cannot be overstated. However, a major limitation is the intolerance of many …
Cobalt‐catalyzed hydrogen‐atom transfer induces bicyclizations that tolerate electron‐rich and electron‐deficient intermediate alkenes
D Vrubliauskas, CD Vanderwal - Angewandte Chemie, 2020 - Wiley Online Library
A novel CoII‐catalyzed polyene cyclization was developed that is uniquely effective when
performed in hexafluoroisopropanol as the solvent. The process is presumably initiated by …
performed in hexafluoroisopropanol as the solvent. The process is presumably initiated by …
Ti (III)-catalyzed cyclizations of ketoepoxypolyprenes: control over the number of rings and unexpected stereoselectivities
SP Morcillo, D Miguel, S Resa… - Journal of the …, 2014 - ACS Publications
We describe a new strategy to control the number of cyclization steps in bioinspired radical
(poly) cyclizations involving epoxypolyenes containing keto units positioned along the …
(poly) cyclizations involving epoxypolyenes containing keto units positioned along the …
Total synthesis of complex terpenoids employing radical cascade processes
K Hung, X Hu, TJ Maimone - Natural product reports, 2018 - pubs.rsc.org
Covering: 2011–2017 Radical cyclizations have a rich history in organic chemistry and have
been particularly generous to the field of natural product synthesis. Owing to their ability to …
been particularly generous to the field of natural product synthesis. Owing to their ability to …
Bioinspired terpene synthesis: a radical approach
This tutorial review highlights the development of radical-based bioinspired synthesis of
terpenes from the initial proposal to the development of modern catalytic methods for …
terpenes from the initial proposal to the development of modern catalytic methods for …
Programmed polyene cyclization enabled by chromophore disruption
MM Solans, VS Basistyi, JA Law… - Journal of the …, 2022 - ACS Publications
A new polyene cyclization strategy exploiting β-ionyl derivatives was developed.
Photoinduced deconjugation of the extended π-system within these chromophores unveils a …
Photoinduced deconjugation of the extended π-system within these chromophores unveils a …
[HTML][HTML] Asymmetric oxidative cation/olefin cyclization of polyenes: Evidence for reversible cascade cyclization
CA Mullen, AN Campbell, MR Gagné - … Chemie (International ed. in …, 2008 - ncbi.nlm.nih.gov
The biosynthesis of cyclic terpenes from polyene precursors by cyclase enzymes is one of
nature's most elegant chemical transformations.[1] The ease with which nature creates …
nature's most elegant chemical transformations.[1] The ease with which nature creates …
Merging chemoenzymatic and radical-based retrosynthetic logic for rapid and modular synthesis of oxidized meroterpenoids
Meroterpenoids are natural products of hybrid biosynthetic origins—derived from both
terpenoid and polyketide pathways—with a wealth of biological activities. Given their …
terpenoid and polyketide pathways—with a wealth of biological activities. Given their …
Exo‐Dig Radical Cascades of Skipped Enediynes: Building a Naphthalene Moiety within a Polycyclic Framework
Cascade radical transformations of acyclic precursors open efficient, convenient and atom‐
economical access to functionalized compounds of increased structural complexity. This …
economical access to functionalized compounds of increased structural complexity. This …
Divergent synthesis of pyrone diterpenes via radical cross coupling
RR Merchant, KM Oberg, Y Lin… - Journal of the …, 2018 - ACS Publications
A divergent strategy for assembling pyrone diterpenes is presented. Capitalizing on the
unique stereo-and chemoselectivity features of radical-based chemistry, the core decalin of …
unique stereo-and chemoselectivity features of radical-based chemistry, the core decalin of …