Studies on the Synthesis of <i>Schisandraceae</i> Natural Products: Exploring a Cyclopropylcarbinol Ring Expansion Strategy

Fischer, Derek; Theodorakis, Emmanuel A.

doi:10.1002/ejoc.200700336

Cited by 36 publications

(11 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…30 Compound 68 presents with a rare C-16/C-17 and C-20/C-21 conjugated double bond and an unusual ester bridge formed between rings A and B, and angustifodilactone A (70) is characterized by a hydroxymethyl at C-25. Schisanbilactones A (72) and B (73) are the rst reported triterpenoids from the stems of S. bicolor. 31 Schisphendilactone A (74) 32 and schinalactone C (75) 33 were isolated from the stems of S. sphenanthera.…”

Section: Structures Classifications and Distributionsmentioning

confidence: 99%

Triterpenoids from the Schisandraceae family: an update

et al. 2015

View full text Add to dashboard Cite

Several significant advances in the field of phytochemistry were made between 2008 and 2014 because of the high level of interest in Schisandraceae triterpenoids. In addition to a dramatic increase in the number of newly identified triterpenoids, the first complete synthesis of a schinortriterpenoid was accomplished. There has also been substantial progress in investigations of biological activity and mechanism of action. In this update, we review more than 250 new triterpenoids and describe their structures, classifications, biogenetic pathways, syntheses, and bioactivities.

show abstract

Section: Structures Classifications and Distributionsmentioning

confidence: 99%

Triterpenoids from the Schisandraceae family: an update

et al. 2015

View full text Add to dashboard Cite

show abstract

“…On the basis of our previously developed cis ‐selective formal [2+2+2]‐dimethylcyclohexanone annulation onto the α,β‐unsaturated ester 11 we have established a trans ‐selective formal [3+1+2]‐dimethylcyclohexanone annulation onto the same α,β‐unsaturated ester 11 . Although a multitude of trans ‐bicyclo[4.4.0]decane‐syntheses exists already, we are aware of no more than quite few precedents, which provide trans ‐fused bicyclo[4.4.0]decanes with a gem ‐dimethyl group at C‐2 and an oxidized carbon substituent at C‐4a′ (both features are present in the bicyclo[4.4.0]decenecarboxylic ester trans ‐ 14a ; Scheme ) directly (which is what our dimethylcyclohexanone annulation does). Examples can be found in the literature.…”

Section: Discussionmentioning

confidence: 94%

Towards a Total Synthesis of Phenalinolactone Core Diterpenoid 6: Synthesis of a Racemic Decahydrobenzocyclobutaisobenzofuran with a trans‐anti‐cis Junction of the Isocyclic Rings

Hampel

Brückner

2017

Eur J Org Chem

View full text Add to dashboard Cite

Synthetic efforts towards the “phenalinolactone core diterpenoid 6” (5) are described. It contains a cyclohexyl alcohol (A ring), a cyclohexane (B ring), and a cyclohexene (C ring), which are angularly annulated trans and cis, respectively. What makes them unique is the trans‐ (or “anti”‐) relationship between the A and the C ring. The trans‐configured A/B ring junction was established in a novel cyclohexanone annulation. Anti‐selective cis‐annulations of the C ring failed when attempted with intramolecular Diels–Alder reactions with dienes of varied electron demand (21, 31). In contrast, an anti‐selective cis‐annulation of a C ring precursor based on an intramolecular [2+2]‐photocycloaddition succeeded. It provided the tetracycle 38 in 70 % yield. It contains a densely functionalized four‐membered ring. It should lend itself to ring‐opening(s) and/or rearrangement(s). Accordingly, compound 38 should be adoptable to proceeding to the target structure 5 in future work.

show abstract

“…The 3-Methyl-phenol is mainly used in pesticides, medicine, perfume, resin plasticizer, film, antioxidant, and reagents [29][30][31]. Cyclopropyl carbinol is an intermediate used in chemical laboratory research and development of organic compounds and pharmaceuticals [32][33][34].…”

Section: The Py-gc-ms Analysismentioning

confidence: 99%

Active components in leaves of Rhus chinensis Mill.

Suo

Sun

Wang³

et al. 2020

THERM SCI

View full text Add to dashboard Cite

Rhus chinensis Mill is a high-quality eco-economic resource for potential sustainable development. To analyze the chemical constituents of extracts from the leaves of Rhus chinensis Mill for resource values, the following analytical methods were performed: Fourier transform infrared (FT-IR) spectrum, gas chromatography-mass spectrometry (GC-MS), thermogravimetry, and pyrolysis-gas chromatography-mass spectrometry (Py-GC-MS). The results showed that the leaves of Rhus chinensis Mill were rich in volatile substances that could be exploited and used.

show abstract

Studies on the Synthesis of Schisandraceae Natural Products: Exploring a Cyclopropylcarbinol Ring Expansion Strategy

Cited by 36 publications

References 28 publications

Triterpenoids from the Schisandraceae family: an update

Triterpenoids from the Schisandraceae family: an update

Towards a Total Synthesis of Phenalinolactone Core Diterpenoid 6: Synthesis of a Racemic Decahydrobenzocyclobutaisobenzofuran with a trans‐anti‐cis Junction of the Isocyclic Rings

Active components in leaves of Rhus chinensis Mill.

Contact Info

Product

Resources

About