Expeditious Synthesis of New 3,4,6‐Trihydroxythiepanes from <scp>d</scp>‐(‐)‐Quinic Acid

Shih, Tzenge‐Lien; Fang, Yi‐Chuan

doi:10.1080/00397910701490113

Cited by 11 publications

(3 citation statements)

References 16 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Shih and coworkers developed a procedure to readily prepare 3,4,6-trihydroxythiepanes from D-(-)-quinic acid (Scheme 31). 82 Scheme 30 Synthesis of oxepanes via functionalized cyclooctatetraene. [79][80][81] Scheme 31 Synthetic route to thiepane via a ring-expansion strategy.…”

Section: Synthesis Of Polyhydroxylated Thiepanesmentioning

confidence: 99%

“…Shih and coworkers developed a procedure to readily prepare 3,4,6-trihydroxythiepanes from d -(–)-quinic acid (Scheme 31). 82 After sequential dihydroxylation and oxidative cleavage of 183 with RuCl 3 and NaIO 4 , and reduction with NaBH 4 gave diol 184 in an 72% yield. After mesylation of 184 to afford bis-mesylate 185 , incorporation of the sulfur with Na 2 S·9H 2 O provides thiepane 186 in a 94% yield.…”

Section: Synthesis Of Polyhydroxylated Thiepanesmentioning

confidence: 99%

See 1 more Smart Citation

Advancements in the synthesis of polyoxygenated oxepanes and thiepanes for applications to natural products

Pote,

Weierbach,

Peczuh

et al. 2024

Org. Chem. Front.

View full text Add to dashboard Cite

show abstract

Section: Synthesis Of Polyhydroxylated Thiepanesmentioning

confidence: 99%

Section: Synthesis Of Polyhydroxylated Thiepanesmentioning

confidence: 99%

Advancements in the synthesis of polyoxygenated oxepanes and thiepanes for applications to natural products

Pote,

Weierbach,

Peczuh

et al. 2024

Org. Chem. Front.

View full text Add to dashboard Cite

show abstract

“…protecting groups, [130][131][132] DDQ-mediated O-debenzylation is often slower. 107,133 The first deprotection attempt on 19 using 3 equivalents of DDQ was difficult to monitor by TLC due to the apparent formation of multiple byproducts. 1 H NMR analysis of the crude reaction mixture after 24 hours indicated only approximately 1:12 conversion based on the integration of the new benzaldehyde peak at 10.03 ppm, relative to the existing benzylic shift at 4.51 ppm.…”

Section: Ddq-mediated Deprotection Attemptsmentioning

confidence: 99%

Investigating Extended Linker Analogues of Risperidone for Treatment of Multiple Sclerosis

Bird¹

View full text Add to dashboard Cite

<p>Risperidone is a second-generation antipsychotic used to treat psychiatric disorders such as schizophrenia, bipolar disorder and autism. It targets dopamine D2 and serotonin 5-HT2A receptors and has immunomodulatory properties. Multiple sclerosis is a chronic inflammatory disease that affects over 2 million people worldwide and currently has no cure. Recent research at Victoria University of Wellington has shown that risperidone is able to reduce disease severity in mouse models of multiple sclerosis. Further research has demonstrated that truncated and unsaturated analogues of risperidone have varying immunomodulatory effects in immune cells. The current research describes the synthesis and preliminary in vitro testing of four extended-linker analogues of risperidone. Structure-activity relationship studies with neurotropic drugs have shown that altering the length of the alkyl chain found in many of these compounds can have significant effects on receptor binding profiles. Synthesis and cytokine production assays of these analogues begin to provide further insight into how risperidone exerts its immunomodulatory effects and may contribute to the development of new treatments for multiple sclerosis.</p>

show abstract

Protection for the Hydroxyl Group, Including 1,2‐ and 1,3‐Diols

2014

Greene's Protective Groups in Organic Synthesis

View full text Add to dashboard Cite

Expeditious Synthesis of New 3,4,6‐Trihydroxythiepanes from d‐(‐)‐Quinic Acid

Cited by 11 publications

References 16 publications

Advancements in the synthesis of polyoxygenated oxepanes and thiepanes for applications to natural products

Advancements in the synthesis of polyoxygenated oxepanes and thiepanes for applications to natural products

Investigating Extended Linker Analogues of Risperidone for Treatment of Multiple Sclerosis

Protection for the Hydroxyl Group, Including 1,2‐ and 1,3‐Diols

Contact Info

Product

Resources

About