Boranes in Organic Chemistry. Part 2. β‐Aminoalkyl‐ and β‐Sulfanylalkylboranes in Organic Synthesis

Dembitsky, Valery M.; Толстиков, Г. А.; Srebnik, Morris

doi:10.1002/chin.200337228

Cited by 4 publications

(6 citation statements)

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“…Halogenated C 15 -acetogenins are widely distributed in red algae Laurencia species . More than 180 compounds have been elucidated since the first discovery of laurencia by the Irie group in 1965 .…”

Section: Introductionmentioning

confidence: 99%

Stereocontrolled Synthesis of a Possible Stereoisomer of Laurenidificin and a Formal Total Synthesis of (+)-Aplysiallene Featuring a Stereospecific Ring Contraction

et al. 2016

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We report a highly stereocontrolled total synthesis of one of the possible stereoisomers of laurenidificin. Highlights of the synthesis include the formation of the 2,6-dioxabicyclo[3.3.0]octane framework by a stereospecific bromolactonization-α-bromination-ring contraction sequence, followed by a stereoselective propargylation, an insertion of the Z-enyne side chain by a hydroindation/cross coupling reaction, and ethylation at C13 with an organocuprate reagent. While the synthetic compound was not identical to the natural product, the absolute stereochemistry of the natural product was proposed on the basis of NMR analyses. Moreover, a formal total synthesis of (+)-aplysiallene was achieved by extending the ring contraction strategy.

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Section: Introductionmentioning

confidence: 99%

Stereocontrolled Synthesis of a Possible Stereoisomer of Laurenidificin and a Formal Total Synthesis of (+)-Aplysiallene Featuring a Stereospecific Ring Contraction

et al. 2016

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“…Halogenated steroids from marine sources have been the subject of extensive research due to their diverse biological activities and potential therapeutic applications. Some of these compounds have demonstrated anti-microbial, anti-viral, anti-inflammatory, and anti-cancer properties [143][144][145][146][147][148][149][150][151][152][153][154][155][156].…”

Section: Steroids Bearing a Halogen Atom (Cl Br Or I)mentioning

confidence: 99%

“…Research on chlorinated plant steroids is still relatively limited compared to other classes of plant steroids. However, some studies have identified and characterized specific chlorinated plant steroids and explored their potential biological activities [145][146][147][148][149][150][151][152][153][154][155][156].…”

Section: Chlorinated Plant Steroidsmentioning

confidence: 99%

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Biological Activity and Structural Diversity of Steroids Containing Aromatic Rings, Phosphate Groups, or Halogen Atoms

Dembitsky

2023

Molecules

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This review delves into the investigation of the biological activity and structural diversity of steroids and related isoprenoid lipids. The study encompasses various natural compounds, such as steroids with aromatic ring(s), steroid phosphate esters derived from marine invertebrates, and steroids incorporating halogen atoms (I, Br, or Cl). These compounds are either produced by fungi or fungal endophytes or found in extracts of plants, algae, or marine invertebrates. To assess the biological activity of these natural compounds, an extensive examination of referenced literature sources was conducted. The evaluation encompassed in vivo and in vitro studies, as well as the utilization of the QSAR method. Numerous compounds exhibited notable properties such as strong anti-inflammatory, anti-neoplastic, anti-proliferative, anti-hypercholesterolemic, anti-Parkinsonian, diuretic, anti-eczematic, anti-psoriatic, and various other activities. Throughout the review, 3D graphs illustrating the activity of individual steroids are presented alongside images of selected terrestrial or marine organisms. Additionally, the review provides explanations for specific types of biological activity associated with these compounds. The data presented in this review hold scientific interest for academic science as well as practical implications in the fields of pharmacology and practical medicine. The analysis of the biological activity and structural diversity of steroids and related isoprenoid lipids provides valuable insights that can contribute to advancements in both theoretical understanding and applied research.

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“…8) Polyacetylene compounds are present in many plants including the Helichrysum genus and display important biological activities. 9,10) H. aureonitens SCH. Bip is a hairy perennial herb which grows mostly in the Kwazulu-Natal province of South Africa 11) and is widely used in folk medicine.…”

mentioning

confidence: 99%

Isolation and Identification of a Novel Chlorophenol from a Cell Suspension Culture of Helichrysum aureonitens

Ziaratnia

Ohyama²,

Hussein

et al. 2009

CHEMICAL & PHARMACEUTICAL BULLETIN

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Boranes in Organic Chemistry. Part 2. β‐Aminoalkyl‐ and β‐Sulfanylalkylboranes in Organic Synthesis

Cited by 4 publications

References 1 publication

Stereocontrolled Synthesis of a Possible Stereoisomer of Laurenidificin and a Formal Total Synthesis of (+)-Aplysiallene Featuring a Stereospecific Ring Contraction

Stereocontrolled Synthesis of a Possible Stereoisomer of Laurenidificin and a Formal Total Synthesis of (+)-Aplysiallene Featuring a Stereospecific Ring Contraction

Biological Activity and Structural Diversity of Steroids Containing Aromatic Rings, Phosphate Groups, or Halogen Atoms

Isolation and Identification of a Novel Chlorophenol from a Cell Suspension Culture of Helichrysum aureonitens

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