Asymmetric synthesis of aerothionin, a marine dimeric spiroisoxazoline natural product, employing optically active spiroisoxazoline derivative

An asymmetric synthesis of highly substituted indenes has been developed via the central–axial–central chirality transfer from optically active propargyl alcohols.

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Asymmetric Synthesis ofα-Methylα-Amino Acids by Diastereoselective Alkylation of Optically Active 6-Isopropyl-3-methyl-2,3—dihydro-6H-1,4-oxazin-2-ones

Angewandte Chemie International Edition in English ◽

10.1002/anie.199709951 ◽

1997 ◽

Vol 36 (9) ◽

pp. 995-997 ◽

Cited By ~ 35

Author(s):

Rafael Chinchilla ◽

Larry R. Falvello ◽

Nuria Galindo ◽

Carmen Nájera

Keyword(s):

Amino Acids ◽

Asymmetric Synthesis ◽

Optically Active

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ChemInform Abstract: Asymmetric Synthesis of Optically Active Alcohols with Two Chiral Centres from a Racemic Aldehyde by the Selective Addition of Dialkylzinc Reagents Using Chiral Catalysts.

ChemInform ◽

10.1002/chin.199147046 ◽

2010 ◽

Vol 22 (47) ◽

pp. no-no

Author(s):

S. NIWA ◽

T. HATANAKA ◽

K. SOAI

Keyword(s):

Asymmetric Synthesis ◽

Optically Active ◽

Chiral Catalysts ◽

Selective Addition

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Asymmetric Synthesis of 3,3′-Piperidinoyl Spirooxindoles and Discovery of Stereospecific Cycloadducts as Novel Hedgehog Pathway Modulators

Synthesis ◽

10.1055/s-0040-1707222 ◽

2020 ◽

Vol 52 (21) ◽

pp. 3140-3152

Author(s):

Kamal Kumar ◽

Mohammad Rehan ◽

Jana Flegel ◽

Franziska Heitkamp ◽

Jorgelina L. Pergomet ◽

...

Keyword(s):

Transition Metal ◽

Small Molecules ◽

Asymmetric Synthesis ◽

Natural Product ◽

Transition Metal Complexes ◽

Alder Reaction ◽

Diels Alder ◽

Hedgehog Pathway ◽

Diels Alder Reaction ◽

Efficient Access

An enantioselective hetero-Diels–Alder reaction of alkylidene oxindoles and 2-aza-3-silyloxy-1,3-butadienes, catalyzed by divalent transition metal complexes with N,N′-dioxide ligands offered an efficient access to natural-product-based 3,3′-piperidinoyl spirooxindole class of small molecules. exo-Cycloadducts formed via stereospecific cycloaddition with Z-olefin displayed potent activity in modulation of hedgehog pathway.

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Asymmetric synthesis. Production of optically active amino acids by catalytic hydrogenation

Journal of the American Chemical Society ◽

10.1021/ja00461a014 ◽

1977 ◽

Vol 99 (19) ◽

pp. 6262-6267 ◽

Cited By ~ 417

Author(s):

M. D. Fryzuk ◽

B. Bosnich

Keyword(s):

Amino Acids ◽

Asymmetric Synthesis ◽

Catalytic Hydrogenation ◽

Optically Active

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Heronapyrrole D: A case of co-inspiration of natural product biosynthesis, total synthesis and biodiscovery

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.10.121 ◽

2014 ◽

Vol 10 ◽

pp. 1228-1232 ◽

Cited By ~ 21

Author(s):

Jens Schmidt ◽

Zeinab Khalil ◽

Robert J Capon ◽

Christian B W Stark

Keyword(s):

Antibacterial Activity ◽

Natural Products ◽

Total Synthesis ◽

Asymmetric Synthesis ◽

Natural Product ◽

Joint Effort ◽

Natural Product Biosynthesis ◽

New Members ◽

Degree Of Oxidation ◽

Rare Class

The heronapyrroles A–C have first been isolated from a marine-derived Streptomyces sp. (CMB-0423) in 2010. Structurally, these natural products feature an unusual nitropyrrole system to which a partially oxidized farnesyl chain is attached. The varying degree of oxidation of the sesquiterpenyl subunit in heronapyrroles A–C provoked the hypothesis that there might exist other hitherto unidentified metabolites. On biosynthetic grounds a mono-tetrahydrofuran-diol named heronapyrrole D appeared a possible candidate. We here describe a short asymmetric synthesis of heronapyrrole D, its detection in cultivations of CMB-0423 and finally the evaluation of its antibacterial activity. We thus demonstrate that biosynthetic considerations and the joint effort of synthetic and natural product chemists can result in the identification of new members of a rare class of natural products.

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