Total synthesis of (+)-(S)-angustureine and the determination of the absolute configuration of the natural product angustureine

Theeraladanon, Chumpol; Arisawa, Mitsuhiro; Nakagawa, Masako; Nishida, Atsushi

doi:10.1016/j.tetasy.2004.12.022

Cited by 60 publications

(30 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For more than ten years, we have been exploring a synthetic methodology for nitrogen-containing heterocycles using these ruthenium carbene catalysts and applying them to the synthesis of biologically active natural products. [11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30] Here, we describe our synthetic study of nitrogen-containing heterocycles using ring-closing metathesis (RCM), such as chiral bicyclic lactams, azacycloundecenes, axially chiral macrolactams, 1,2-dihydroquinolines and indoles, including the development of silyl-enol ether ene metathesis and selective isomerization of terminal olefin, and its application to the synthesis of the natural products, (Ϫ)-coniceine, (S)-pyrrolam A and angustureine.…”

Section: Development Of Syntheticmentioning

confidence: 99%

“…Axially Chiral Macrolactams 14,17) : We recently reported that new axially chiral ligands, 1,1Ј-(2,2Ј-bisacylamino)binaphthalenes (BINAMIDE), are effective in the ytterbium-catalyzed asymmetric Diels-Alder reaction between cyclopentadiene and crotonyl-1,3-oxazolidin-2-one (Chart 4). 53) 1,1Ј-(2,2Ј-Bisacylamino)binaphthalenes (23)(24)(25) were synthesized by reacting binaphthyldiamine with mixed anhydride of the corresponding acid, and then reacting the product with ruthenium carbene catalyst (D) under various conditions (Table 4).…”

Section: Mitsuhiro Arisawa Was Born In 1971 Inmentioning

confidence: 99%

“…Total synthesis of angustureine and determination of its absolute structure 24) : A novel 2-substituted quinoline alkaloid, angusturiene, was isolated from Galipea officinalis HANCOCK by Jacquemond-Collet et al in 1999.…”

Section: Mitsuhiro Arisawa Was Born In 1971 Inmentioning

confidence: 99%

See 2 more Smart Citations

Development of Environmentally Benign Organometallic Catalysis for Drug Discovery and Its Application

Arisawa

2007

CHEMICAL & PHARMACEUTICAL BULLETIN

Self Cite

View full text Add to dashboard Cite

We have developed a novel organometallic catalysis and applied it to drug discovery. Two new catalysts were found, ruthenium hydride with a nitrogen-containing heterocyclic carbene (A) and an organopalladium catalyst supported on a sulfur-terminated semiconductor, gallium arsenide (001) (B). Both catalysts are environmentally benign, because A can yield indole derivatives with good atom economy, and B can catalyze the Mizoroki-Heck reaction more than 10 times with only trace amounts of leached palladium (ppb level). We also describe our synthetic study of nitrogen-containing heterocycles using ring-closing metathesis (RCM), such as chiral bicyclic lactams, azacycloundecenes, axially chiral macrolactams, 1,2-dihydroquinolines and indoles, including the development of silyl-enol ether ene metathesis, selective isomerization of terminal olefin, enamide metathesis and cycloisomerization and its application to the syntheis of 4 natural products, (؊)-coniceine, (S)-pyrrolam A, angustureine, and fistulosin.

show abstract

Section: Development Of Syntheticmentioning

confidence: 99%

Section: Mitsuhiro Arisawa Was Born In 1971 Inmentioning

confidence: 99%

See 1 more Smart Citation

Development of Environmentally Benign Organometallic Catalysis for Drug Discovery and Its Application

Arisawa

2007

CHEMICAL & PHARMACEUTICAL BULLETIN

Self Cite

View full text Add to dashboard Cite

show abstract

“…[7][8] In the literature, numerous methods describe the synthesis of 1,2-dihydroquinolines. Typically aryl amines were reacted with a range of different compounds such as ketones, 9 α,β-unsaturated ketones 10 , 2,2-dimethoxy propane, 11 aldehyde, 12 alkynes, 13 alcohol, 14 glycerine, 15 α-ketoester [16][17] in the presence of Lewis acid or Brønsted acid catalysts. To date there have been few methods published for the synthesis of 1,2-dihydroquinoline derivatives using α-ketoesters.…”

Section: Introductionmentioning

confidence: 99%

An efficient method for the preparation of 2,2,4-trisubstituted 1,2-dihydroquinolines using catalytic amount Bi(OTf)3 as catalyst

Gültekin¹,

Frey²

2012

Arkivoc

View full text Add to dashboard Cite

Substituted 1,2-dihydroquinolines have been synthesised from substituted anilines and methyl pyruvate using catalytic amounts of commercially available Bi(OTf) 3 as a catalyst under microwave-assisted conditions. This method is simple, easy to work up, inexpensive, with a broad substrate scope and short reaction times. The reaction provides 1,2-dihydroquinolines (19 examples) in good yields (34-97% yields).

show abstract

“…With the RCM precursor in hand, subjection to [Ru]-II catalyst (CH 2 Cl 2 , 50 • C) gave quinoline 265 in 92% yield. Finally, hydrogenation, deprotection, and subsequent methylation provided (+)-(S)-angustureine (266) in 68% yield (Scheme 2.58)[86].…”

mentioning

confidence: 99%

Natural Products Containing Medium‐Sized Nitrogen Heterocycles Synthesized by Ring‐Closing Alkene Metathesis

Broek

Meeuwissen

Delft

et al. 2010

Metathesis in Natural Product Synthesis

View full text Add to dashboard Cite

The formation of carbon-carbon bonds is a crucial issue in organic synthesis. Out of all methodologies available, the metathesis reaction has, over the past decade, evolved as one of the most useful tools in this field to rapidly construct the skeleton of carba-and heterocyclic molecules [1]. Key step of the metathesis reaction entails the metal-catalyzed redistribution of two carbon-carbon double bonds by a scission-recombination process [2]. Among various applications of the metathesis reaction, ring-closing metathesis (RCM) has emerged as one of the most powerful tools for the construction of natural and unnatural cyclic compounds (Scheme 2.1) [3]. Other types of metathesis reactions developed so far include cross-metathesis (CM), ring-opening metathesis (ROM), ring rearrangement metathesis (RRM, combining ROM with RCM in a tandem sequence), and ene-yne metathesis [3].The metathesis reaction has already been used for several decades in polymer chemistry for ring-opening metathesis polymerization (ROMP) [4]. Only since the development of well-defined molybdenum and ruthenium carbene complexes by Schrock [5] and Grubbs [6] in 1990 and 1992, respectively, an explosion of their application in organic synthesis has been witnessed. Initially, it was demonstrated that the Schrock catalyst [Mo]-I could serve as a homogeneous catalyst for olefin RCM [7]. Unfortunately, metal carbene complex [Mo]-

show abstract

Total synthesis of (+)-(S)-angustureine and the determination of the absolute configuration of the natural product angustureine

Cited by 60 publications

References 24 publications

Development of Environmentally Benign Organometallic Catalysis for Drug Discovery and Its Application

Development of Environmentally Benign Organometallic Catalysis for Drug Discovery and Its Application

An efficient method for the preparation of 2,2,4-trisubstituted 1,2-dihydroquinolines using catalytic amount Bi(OTf)3 as catalyst

Natural Products Containing Medium‐Sized Nitrogen Heterocycles Synthesized by Ring‐Closing Alkene Metathesis

Contact Info

Product

Resources

About