Total synthesis of fuligocandines A and B

Pettersson, B.; Hasimbegovic, Vedran; Bergman, Jan

doi:10.1016/j.tetlet.2009.10.134

Cited by 16 publications

(12 citation statements)

References 11 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…2 Prompted by this interesting biological activity and our ongoing interest in cycloanthranilylproline-derived natural products we aimed at developing practical syntheses of both fuligocandin A and B. 3 In addition to having the tricyclic cycloanthraniloproline core structure, both fuligocandin A and B contain a vinylogous amide function ( Figure 1). Vinylogous amides are versatile reactants; i. e., they can act as ambient electrophiles but also as nucleophiles and are, furthermore, able to participate in pericyclic and radical processes, properties which endow them as valuable intermediates for synthesis of, e.g., natural products.…”

Section: ' Introductionmentioning

confidence: 99%

“…Under the conditions employed (DABCO, P(OMe) 3 , 90°C) that successfully gave fuligocandin A, the indole N-protecting group was also removed; however, the racemic fuligocandin B was never isolated in more than 20% yield. Remarkably, TLC analysis during the alkylation step indicated that the episulfide contraction of the alkylated intermediate 14b proceeded very rapidly in hot DMSO in the absence of both base and thiophile to give the N-protected fuligocandin B 15b in 57% isolated yield.…”

Section: ' Introductionmentioning

confidence: 99%

See 1 more Smart Citation

One-Pot Eschenmoser Episulfide Contractions in DMSO: Applications to the Synthesis of Fuligocandins A and B and a Number of Vinylogous Amides

2011

Self Cite

View full text Add to dashboard Cite

show abstract

Section: ' Introductionmentioning

confidence: 99%

Section: ' Introductionmentioning

confidence: 99%

One-Pot Eschenmoser Episulfide Contractions in DMSO: Applications to the Synthesis of Fuligocandins A and B and a Number of Vinylogous Amides

2011

Self Cite

View full text Add to dashboard Cite

show abstract

“…in 2009, using the aza‐Wittig method . A practical racemic first total synthesis of fuligocandin B ( 2 ) was achieved by Bergman and co‐workers in 2010, using Eschenmoser episulfide contraction as the key step. We also achieved a total synthesis of fuligocandin A ( 1 ) and B ( 2 ) with moderate enantiomeric excess ( 1 ; 70 % ee , 2 ; 61 % ee ) .…”

Section: Resultsmentioning

confidence: 99%

Valosin‐containing Protein is a Target of 5′‐l Fuligocandin B and Enhances TRAIL Resistance in Cancer Cells

et al. 2016

View full text Add to dashboard Cite

Fuligocandin B (2) is a novel natural product that can overcome TRAIL resistance. We synthesized enatiomerically pure fuligocandin B (2) and its derivative 5′‐I fuligocandin B (4), and found that the latter had an improved biological activity against the human gastric cancer cell line, AGS. We attached a biotin linker and photoactivatable aryl diazirine group to 5′‐I fuligocandin B (4), and employed a pull‐down assay to identify valosin‐containing protein (VCP/p97), an AAA ATPase, as a 5′‐I fuligocandin B (4) target protein. Knock‐down of VCP by siRNA enhanced sensitivity to TRAIL in AGS cells. In addition, 4 enhanced CHOP and DR5 protein expression, and overall intracellular levels of ubiquitinated protein. These data suggest that endoplasmic reticulum stress caused through VCP inhibition by 4 increases CHOP‐mediated DR5 up‐regulation, which enhances TRAIL‐induced cell death in AGS cells. To the best of our knowledge, this is the first example to show a relationship between VCP and TRAIL‐resistance‐overcoming activity in cancer cells.

show abstract

“…Bearing an active enone fragment, indolylvinyl ketones can be utilized as versatile building blocks for the construction of new complex structures containing an indole subunit. They were employed as precursors of fuligocandin B, 4 (±)-6,7-secoagroclavine, 5 hapalindole J, 6 isocryptolepine and its derivatives, 7 ergot alkaloids, 8 murrapanine, 9 and flinderole C analogues, 10 and many other valuable bioactive molecules.…”

Section: Introductionmentioning

confidence: 99%

Indolylvinyl Ketones: Building Blocks for the Synthesis of Natural Products and Bioactive Compounds

et al. 2019

View full text Add to dashboard Cite

Indolylvinyl ketones are valuable building blocks that can be utilized for the synthesis of numerous natural products and bioactive molecules containing an indole core motif. Herein, we describe their application for the total synthesis of some alkaloids, their analogues, and a variety of other important compounds, with an emphasis on biologically active examples.1 Introduction2 Functionalization of the Enone C=C Bond2.1 Reduction2.2 Michael Addition2.3 Cycloaddition3 Transformation of the Carbonyl Group3.1 Reduction3.2 Knoevenagel Reaction3.3 Addition of Organometallic Compounds3.4 Olefination4 Reactions Involving the Enone Conjugate System С=С–С=О4.1 Reactions with 1,2-Dinucleophiles4.2 Reactions with Compounds Bearing an Active Methylene Group4.3 Reactions with 1,3-Dinucleophiles4.4 Reactions with 1,4-Dinucleophiles5 Functionalization of the Enone Methylene Group C(O)–CH2R5.1 Acylation/Crotonic Condensation and Related Transformations5.2 Enolization6 Functionalization of the Indole Core6.1 [4+2] Cycloaddition6.2 [3+3] Annulation6.3 Electrocyclic Reactions7 Miscellaneous8 Conclusions

show abstract

Total synthesis of fuligocandines A and B

Cited by 16 publications

References 11 publications

One-Pot Eschenmoser Episulfide Contractions in DMSO: Applications to the Synthesis of Fuligocandins A and B and a Number of Vinylogous Amides

One-Pot Eschenmoser Episulfide Contractions in DMSO: Applications to the Synthesis of Fuligocandins A and B and a Number of Vinylogous Amides

Valosin‐containing Protein is a Target of 5′‐l Fuligocandin B and Enhances TRAIL Resistance in Cancer Cells

Indolylvinyl Ketones: Building Blocks for the Synthesis of Natural Products and Bioactive Compounds

Contact Info

Product

Resources

About