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 …

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 …

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 …

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 …

Bioinspired terpene synthesis: a radical approach

J Justicia, LA de Cienfuegos, AG Campana… - Chemical Society …, 2011 - pubs.rsc.org
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 …

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 …

[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 …

Merging chemoenzymatic and radical-based retrosynthetic logic for rapid and modular synthesis of oxidized meroterpenoids

J Li, F Li, E King-Smith, H Renata - Nature chemistry, 2020 - nature.com
Meroterpenoids are natural products of hybrid biosynthetic origins—derived from both
terpenoid and polyketide pathways—with a wealth of biological activities. Given their …

ExoDig Radical Cascades of Skipped Enediynes: Building a Naphthalene Moiety within a Polycyclic Framework

K Pati, AM Hughes, H Phan… - Chemistry–A European …, 2014 - Wiley Online Library
Cascade radical transformations of acyclic precursors open efficient, convenient and atom‐
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 …