Stereocontrolled synthesis of contignasterol's side chain

Izzo, Irene; Pironti, Vincenza; Monica, Carmela Della; Sodano, G.; Riccardis, Francesco De

doi:10.1016/s0040-4039(01)01964-5

Cited by 11 publications

(10 citation statements)

References 18 publications

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“…We theorized that target compounds 2-7 could be retrosynthetically disconnected into three distinct fragments 8, 29-31 9, 32 and 10 (or 11 [33][34][35] ). The former motifs 8 and 9, which were used to construct the steroid aglycon via a dimethylaluminum chloride-mediated 'ene' reaction, 31 could be formed, respectively, from commercial R-(+)-limonene and dehydroisoandrosteron through a sequence of reactions. The D-xylopyranosyl trichloroacetimidates 10 and 11 were obtained from D-xylose in a straightforward manner.…”

Section: Resultsmentioning

confidence: 99%

“…The synthesis of the side chain aldehyde 8 [29][30][31] was commenced from commercially available R-(+)-limonene, which was readily converted to R-menthene 12 in the presence of PtO 2 through a selective hydrogenation. Cleavage of the cyclic double bond of 12 proceeded by O 3 -catalyzed oxidation and in situ protection of the resulting unstable aldehyde with Me 2 S. The keto-acetal 13 was treated by 3% HClO 4 in THF-H 2 O to form the corresponding keto-aldehyde, which was selectively reduced with lithium tris[(3-ethyl-3-pentyl)oxy]aluminohydride (LiAl(OCEt 3 ) 3 ) in THF affording the keto-alcohol 14.…”

Section: Resultsmentioning

confidence: 99%

“…Protection of the primary OH with a TBDPS group using TBDPSCl in DMF followed by Baeyer-Villiger reaction with mCPBA in CH 2 Cl 2 furnished 16 in 85% yield. Removal of the TBDPS group employing tetrabutylammonium fluoride (TBAF) in THF followed by reaction with Dess-Martin periodinane afforded the side chain aldehyde 8 in 97% yield, which all intermediates 12-17 are known compounds [29][30][31] (Scheme 2). The synthesis of block 9 was achieved in a two-step sequence 32 starting from the industrial material dehydroisoandrosteron in excellent yield (Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

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Synthesis of analogues of linckoside B, a new neuritogenic steroid glycoside

Liu

Wang

et al. 2013

New J. Chem.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Synthesis of analogues of linckoside B, a new neuritogenic steroid glycoside

Liu

Wang

et al. 2013

New J. Chem.

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“…Marine sponges have recently been recognized as a source of uncommon steroids showing potent biological anti-inflammatory activities. Contignasterol is a natural polyoxygenated steroid, isolated from the marine sponge, Petrosia contignata , in Papua New Guinea [ 32 ]. It presents a particular chemical structure with a new side chain and with an unusual set of functional groups [ 33 ].…”

Section: Marine Natural Products: a Potential Immunomodulating Andmentioning

confidence: 99%

Marine Bioactives and Potential Application in Sports

et al. 2014

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An enriched diet with antioxidants, such as vitamin E, vitamin C, β-carotene and phenolic compounds, has always been suggested to improve oxidative stress, preventing related diseases. In this respect, marine natural product (MNP), such as COX inhibitors, marine steroids, molecules interfering with factors involved in the modulation of gene expression (such as NF-κB), macrolides, many antioxidant agents, thermogenic substances and even substances that could help the immune system and that result in the protection of cartilage, have been recently gaining attention. The marine world represents a reserve of bioactive ingredients, with considerable potential as functional food. Substances, such as chitin, chitosan, n-3 oils, carotenoids, vitamins, minerals and bioactive peptides, can provide several health benefits, such as the reduction of cardiovascular diseases, anti-inflammatory and anticarcinogenic activities. In addition, new marine bioactive substances with potential anti-inflammatory, antioxidant and thermogenic capacity may provide health benefits and performance improvement, especially in those who practice physical activity, because of their increased free radical and Reacting Oxygen Species (ROS) production during exercise, and, particularly, in athletes. The aim of this review is to examine the potential pharmacological properties and application of many marine bioactive substances in sports.

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“…This natural polyoxygenated steroid with a new side chain, isolated from the marine sponge Petrosia contignata in Papua New Guinea, has been the subject of many investigations, including both biological studies and synthetic work [ 52 ].…”

Section: Biology Of Marine Natural Products: a Potential Anti-inflmentioning

confidence: 99%

Marine Bioactives: Pharmacological Properties and Potential Applications against Inflammatory Diseases

et al. 2012

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Inflammation is a hot topic in medical research, because it plays a key role in inflammatory diseases: rheumatoid arthritis (RA) and other forms of arthritis, diabetes, heart diseases, irritable bowel syndrome, Alzheimer’s disease, Parkinson’s disease, allergies, asthma, even cancer and many others. Over the past few decades, it was realized that the process of inflammation is virtually the same in different disorders, and a better understanding of inflammation may lead to better treatments for numerous diseases. Inflammation is the activation of the immune system in response to infection, irritation, or injury, with an influx of white blood cells, redness, heat, swelling, pain, and dysfunction of the organs involved. Although the pathophysiological basis of these conditions is not yet fully understood, reactive oxygen species (ROS) have often been implicated in their pathogenesis. In fact, in inflammatory diseases the antioxidant defense system is compromised, as evidenced by increased markers of oxidative stress, and decreased levels of protective antioxidant enzymes in patients with rheumatoid arthritis (RA). An enriched diet containing antioxidants, such as vitamin E, vitamin C, β-carotene and phenolic substances, has been suggested to improve symptoms by reducing disease-related oxidative stress. In this respect, the marine world represents a largely untapped reserve of bioactive ingredients, and considerable potential exists for exploitation of these bioactives as functional food ingredients. Substances such as n -3 oils, carotenoids, vitamins, minerals and peptides provide a myriad of health benefits, including reduction of cardiovascular diseases, anticarcinogenic and anti-inflammatory activities. New marine bioactives are recently gaining attention, since they could be helpful in combating chronic inflammatory degenerative conditions. The aim of this review is to examine the published studies concerning the potential pharmacological properties and application of many marine bioactives against inflammatory diseases.

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Stereocontrolled synthesis of contignasterol's side chain

Cited by 11 publications

References 18 publications

Synthesis of analogues of linckoside B, a new neuritogenic steroid glycoside

Synthesis of analogues of linckoside B, a new neuritogenic steroid glycoside

Marine Bioactives and Potential Application in Sports

Marine Bioactives: Pharmacological Properties and Potential Applications against Inflammatory Diseases

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