[2.2.2]- to [3.2.1]-Bicycle Skeletal Rearrangement Approach to the Gibberellin Family of Natural Products

Smith, Brandon R.; Njardarson, Jón T.

doi:10.1021/acs.orglett.8b01031

Cited by 9 publications

(3 citation statements)

References 32 publications

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“…Gibberellic acids are ent -kaurene metabolites that have undergone a C-8 migration from C-7 to C-6, with conservation of the challenging bicyclo[3.2.1]octane core (Figure ). Very recently, Njardarson reported another concise racemic entry to the gibberellane core requiring only 9 steps, using an intramolecular Diels–Alder reaction to establish a [2.2.2]bicycle which can be rearranged to a [3.2.1]bicyclic system via a 1,2- (or 1,5-) carbon shift (Scheme d). We now report our own synthetic studies in this field, aiming at a direct elaboration of the [3.2.1]bicyclic system via an intramolecular (4 + 3) cycloaddition (Schemes e and ) .…”

supporting

confidence: 56%

An Intramolecular Cycloaddition Approach to the Kauranoid Family of Diterpene Metabolites

et al. 2018

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Synthetic studies toward the ent-kauranoid family of diterpene natural products are reported. An intramolecular (4 + 3) cycloaddition allows the direct elaboration of diverse natural product frameworks, encompassing a challenging bicyclo[3.2.1]octane core. The established routes comprise only a few synthetic operations (3−5 steps), transforming a range of simple starting materials into the tetracyclic scaffolds that are commonly found in many ent-kaurene metabolites.

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supporting

confidence: 56%

An Intramolecular Cycloaddition Approach to the Kauranoid Family of Diterpene Metabolites

et al. 2018

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“…More than 130 GA have been reported in plants, fungi, and bacteria to date [13]. They are mostly biologically inactive and act as precursors for bioactive GAs, including GA1, GA3, GA4, and GA7 [14].…”

Section: Gibberellin Biosynthesis and Deactivation Pathwaysmentioning

confidence: 99%

Manipulating GA-Related Genes for Cereal Crop Improvement

Cheng

Hill

Shabala

et al. 2022

IJMS

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The global population is projected to experience a rapid increase in the future, which poses a challenge to global food sustainability. The “Green Revolution” beginning in the 1960s allowed grain yield to reach two billion tons in 2000 due to the introduction of semi-dwarfing genes in cereal crops. Semi-dwarfing genes reduce the gibberellin (GA) signal, leading to short plant stature, which improves the lodging resistance and harvest index under modern fertilization practices. Here, we reviewed the literature on the function of GA in plant growth and development, and the role of GA-related genes in controlling key agronomic traits that contribute to grain yield in cereal crops. We showed that: (1) GA is a significant phytohormone in regulating plant development and reproduction; (2) GA metabolism and GA signalling pathways are two key components in GA-regulated plant growth; (3) GA interacts with other phytohormones manipulating plant development and reproduction; and (4) targeting GA signalling pathways is an effective genetic solution to improve agronomic traits in cereal crops. We suggest that the modification of GA-related genes and the identification of novel alleles without a negative impact on yield and adaptation are significant in cereal crop breeding for plant architecture improvement. We observed that an increasing number of GA-related genes and their mutants have been functionally validated, but only a limited number of GA-related genes have been genetically modified through conventional breeding tools and are widely used in crop breeding successfully. New genome editing technologies, such as the CRISPR/Cas9 system, hold the promise of validating the effectiveness of GA-related genes in crop development and opening a new venue for efficient and accelerated crop breeding.

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“…Cyclohexadienones continue to serve as useful reactive intermediates and building blocks for organic synthesis , and medicinal chemistry . Interest in these compounds stems from their dense functionality and the fully substituted carbon atom that is necessarily present.…”

Section: Introductionmentioning

confidence: 99%

New Strategy To Access Enantioenriched Cyclohexadienones: Kinetic Resolution of para-Quinols by Organocatalytic Thiol-Michael Addition Reactions

et al. 2018

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Existing stereoselective routes to 2,5-cyclohexadienones involve either desymmetrization of an achiral substrate or have attempted to perform an asymmetric dearomatization of a phenol. Herein, we report proof-of-principle experiments aimed at developing a kinetic resolution as an alternative method for accessing enantioenriched 2,5-cyclohexadienones. More specifically, chiral bifunctional thiourea catalysts were used to promote the addition of 2-thionapthalene into unsymmetric para -quinols. The selectivity of the kinetic resolution was found to be quite sensitive to substitution around the substrate.

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[2.2.2]- to [3.2.1]-Bicycle Skeletal Rearrangement Approach to the Gibberellin Family of Natural Products

Cited by 9 publications

References 32 publications

An Intramolecular Cycloaddition Approach to the Kauranoid Family of Diterpene Metabolites

An Intramolecular Cycloaddition Approach to the Kauranoid Family of Diterpene Metabolites

Manipulating GA-Related Genes for Cereal Crop Improvement

New Strategy To Access Enantioenriched Cyclohexadienones: Kinetic Resolution of para-Quinols by Organocatalytic Thiol-Michael Addition Reactions

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