Total syntheses of schilancidilactones A and B, schilancitrilactone A, and 20-epi-schilancitrilactone A via late-stage nickel-catalyzed cross coupling

Wang, Hengtao; Zhang, Xiunan; Tang, Pingping

doi:10.1039/c7sc03293e

Cited by 31 publications

(14 citation statements)

References 64 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…In an extension to their total synthesis of schilancitrilactone A, [47a] Tang and co‐workers have completed the syntheses of schilancitrilactones B, C ( 172 , 173 ) [47b] and schilancidilactones A, B ( 174 , 175 ) [47b,c] by taking advantage of common retrosynthetic building blocks (Scheme 18). [47b,c] A gem ‐dimethyl iodolactone 176 derived from (−)‐carvone was condensed with the furofuranone aldehyde 177 to yield the enone adduct 178 .…”

Section: Total Synthesis Of Furo[23‐b]furanone Natural Products (Typmentioning

confidence: 99%

Progress in the Total Synthesis of Natural Products Embodying Diverse Furofuranone Motifs: A New Millennium Update

2020

View full text Add to dashboard Cite

Complex, functionally embellished natural products embodying diverse, oxygen rich furofuranone fragments like furo[3,4-c]furanone, furo[2,3-b]furanone, furo[3,4-b]furan-2(3H)-one, furo[3,4-b]furan-4(2H)-one and furo[3,4-b]furan-6(4H)-one as the key motif and displaying wide range of biological activities such as anti-cancer, anti-HIV, anti-microbial activities, etc., continue to draw considerable traction towards targeted synthesis, methodolgical developments as well as medicinal chemistry guided efforts. The challenging and tempting combination of complexity laden architecture and varied bioactivity profile, among the variegated furofuranone natural products has led to intense synthetic activity in the arena in recent years and culminated in the total synthesis of structurally diverse family of bioactive metabolites such as gracilioethers, syringolides, degraded spongianes etc. While comprehensively recounting the attainments in the total syntheses of furofuranone natural products in the past two decades (in the 21st century), this review attempts to identify the key tactics deployed in each synthetic campaign. This topical review aims at drawing and sustaining the interest of synthetic chemistry community in undertaking further creative pursuits towards this rich and enticing family of natural products while concurrently exploring the utility driven diversity space around them. Scheme 2. Pattenden's synthesis of (�)-anthecularin (ref. 11) Scheme 3. Watanabe's synthesis of (+)-anthecularin (ref. 12

show abstract

Section: Total Synthesis Of Furo[23‐b]furanone Natural Products (Typmentioning

confidence: 99%

Progress in the Total Synthesis of Natural Products Embodying Diverse Furofuranone Motifs: A New Millennium Update

2020

View full text Add to dashboard Cite

show abstract

“…A biosynthetic pathway starting from a 3,4‐ seco ‐cycloartane triterpenoid has been proposed for 253 . In 2017, Tang and co‐workers reported the first and only total synthesis of this exotic nortriterpenoid (Scheme ) . According to their retrosynthetic analysis, the iodoethyl lactone 347 and the furo[2,3‐ b ]furanone aldehyde 348 were the primary targets for synthesis.…”

Section: Total Synthesis Of Furo[32‐b]furanone Natural Productsmentioning

confidence: 99%

Recent Advances in Total Synthesis of Bioactive Furo[3,2‐b]furanone Natural Products

et al. 2020

View full text Add to dashboard Cite

The ubiquitous presence of highly oxygenated furo[3,2‐b]furanone fragments in diverse natural products with wide range of biological activities such as anti‐cancer, anti‐HIV, anti‐microbial activities, etc., has augmented their appeal both for synthetic and medicinal chemistry campaigns. Enticed by their potent biological activities and challenging polycyclic architecture, total synthesis of furo[3,2‐b]furanone natural products has witnessed intense activity in recent years with many notable achievements in the synthesis of structurally embellished family of bioactive metabolites such as plakortones, lactonamycines, schisanartanes, etc. While presenting a comprehensive account of post‐2000 syntheses of these natural products, through strategic and nuanced use of modern tools of organic synthesis, this review also aims to stimulate interest in exploring the diversity space around these natural products for newer applications.

show abstract

“…4,5 Since the isolation in 2003 of the first schinortriterpenoid, these compounds have attracted much attention from the organic synthesis community. 6 To date, the total syntheses of 12 schinortriterpenoids have been reported by our research laboratory (Figure 1) 7,12−14 or others including the groups of Li, 8,10 Anderson, 9 Tang, 11,15 and Ding 16 (Figure 3).…”

Section: ■ Introductionmentioning

confidence: 99%

“…Structurally unique and challenging natural products are always a source of inspiration for synthetic chemists to design and develop new chemistry to map out the relations among the chemical structure, reactivity, reaction pathways, and reaction mechanism. , Since the isolation in 2003 of the first schinortriterpenoid, these compounds have attracted much attention from the organic synthesis community . To date, the total syntheses of 12 schinortriterpenoids have been reported by our research laboratory (Figure ) ,− or others including the groups of Li, , Anderson, Tang, , and Ding (Figure ).…”

Section: Introductionmentioning

confidence: 99%

The Journey of Schinortriterpenoid Total Syntheses

Yang

2019

Acc. Chem. Res.

View full text Add to dashboard Cite

CONSPECTUS: Plants in the Schisandraceae family are important components of the traditional Chinese herbal medicines and are often used to treat various illnesses. Therefore, these Schisandraceae plants are valuable sources for the discovery of new chemical entities for novel therapeutic development. Considerable progress has been made in the identification of bioactive and structurally novel triterpenoids from the Schisandraceae family in the past two decades. In particular, Sun and co-workers have successfully isolated over 100 nortriterpenoids from the Schisandraceae family. Some of these nortriterpenoids have strong inhibitory activities toward hepatitis, tumors, and HIV-1. However, the natural scarcity of these nortriterpenoids in the Schisandraceae plants has hampered their isolation and further biomedical development, and their biosynthesis has not been fully elucidated. It is therefore important and urgent to develop efficient and streamlined total syntheses of these medicinally important nortriterpenoids. Such syntheses will provide sufficient materials for detailed biological studies as well as new synthetic analogues and probe molecules to improve their biological functions and elucidate their mode of actions. However, because of their structural novelty and complexity, the total syntheses of these nortriterpenoid natural products present a significant challenge for synthetic chemists, despite the progress made in organic synthesis, particularly total synthesis, in the 20th century and since the beginning of the 21st century. New synthetic methodologies and strategies therefore need to be invented and developed to facilitate the total syntheses of these nortriterpenoid natural products. With this in mind, our group has spent the last 15 years, ever since the isolation of micrandilactone A (1) by Sun and co-workers in 2003 (Sun et al. Org. Lett. 2003, 5, 1023−1026, working on synthetic studies with a view to developing methods and strategies for the total syntheses of schinortriterpenoids. Enabling methods such as a thiourea/Pd-catalyzed alkocycarbonylative annulation and a thiourea/Co-catalyzed Pauson−Khand reaction have been developed under these circumstances to form the key ring systems and stereocenters of these complex target molecules. These methodological advances have led us to the first total syntheses of schindilactone A (2), lancifodilactone G acetate (6a), 19-dehydroxyarisandilactone A (9), and propindilactone G (10) with diverse structural features via a branchingoriented strategy. The chemistry developed during our total synthesis campaign has not only helped us to deal with various challenges encountered in the syntheses of the four target molecules, but has also opened up new avenues for synthesizing other naturally occurring schinortriterpenoids and their derivatives, which will likely result in molecules with improved biological functions and tool compounds to enable elucidation of their mechanism of actions or potential cellular targets. This Account highlights the chemistry evolutio...

show abstract

Total syntheses of schilancidilactones A and B, schilancitrilactone A, and 20-epi-schilancitrilactone A via late-stage nickel-catalyzed cross coupling

Abstract: The first total syntheses of schilancidilactones A and B, schilancitrilactone A, and 20-epi-schilancitrilactone A have been accomplished.

Cited by 31 publications

References 64 publications

Progress in the Total Synthesis of Natural Products Embodying Diverse Furofuranone Motifs: A New Millennium Update

Progress in the Total Synthesis of Natural Products Embodying Diverse Furofuranone Motifs: A New Millennium Update

Recent Advances in Total Synthesis of Bioactive Furo[3,2‐b]furanone Natural Products

The Journey of Schinortriterpenoid Total Syntheses

Contact Info

Product

Resources

About