Efficient total synthesis of AI-77-B, A gastroprotective substance from bacillus pumilus AI-77

Hamada, Y.; Hara, Osamu; Kawai, Akiyoshi; Kohno, Yasushi; Shioiri, Takayuki

doi:10.1016/s0040-4020(01)82406-6

Cited by 85 publications

(24 citation statements)

References 26 publications

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“…Fractions corresponding to the major absorbance peak (20 to 22 min) were pooled, the solvent was extracted, and the product was dissolved in 0.6 ml of deuterated dimethyl sulfoxide (DMSOd 6 (16). Approximately 20 mg of 6-methylsalicylic acid was produced from 12 agar plates (a total of 300 ml of medium), an amount comparable to the highest yields for actinomycete polyketide production in the plasmid expression system in CH999.…”

Section: Vol 177 1995 Notes 4545mentioning

confidence: 99%

Expression of a functional fungal polyketide synthase in the bacterium Streptomyces coelicolor A3(2)

et al. 1995

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The multifunctional 6-methylsalicylic acid synthase gene from Penicillium patulum was engineered for regulated expression in Streptomyces coelicolor. Production of significant amounts of 6-methylsalicylic acid by the recombinant strain was proven by nuclear magnetic resonance spectroscopy. These results suggest that it is possible to harness the molecular diversity of eukaryotic polyketide pathways by heterologous expression of biosynthetic genes in an easily manipulated model bacterial host in which prokaryotic aromatic and modular polyketide synthase genes are already expressed and recombined.

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Section: Vol 177 1995 Notes 4545mentioning

confidence: 99%

Expression of a functional fungal polyketide synthase in the bacterium Streptomyces coelicolor A3(2)

et al. 1995

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“…The absolute configuration of 1 was determined from spectral data and by X-ray diffraction studies together with chemical studies [4]. This new class of antiulcer agents led Shioiri and coworkers [5] to complete the first total synthesis of AI-77-B ((-)-1) in 1989 by coupling the aminodihydroisocoumarin (-)-2 to the partially protected (2S,3S,4S)-4-amino-5-cyano-2,3-dihydroxypentanoic-acid derivative 3 (see Scheme I ); the latter was The reaction of (&)-18a with benzotriazol-1-01 (BtOH) and dicyclohexylcarbodiimide (DCC) in CH,Cl,/DMF 3 : 1 (OO, 20 min) followed by the addition of 1 equiv. of (-)-2 (prepared according to [5]) and of Et,N in CH,Cl,/DMF 3 : 1 led to a 1 : 1 mixture of the corresponding amides (-)-20 and (-)-21 which were readily separated and purified by flash column chromatography (FC) on silica gel (35 and 36% yield, resp.…”

Section: Chlorobenzoyl)-23-dideoxy-a -Dl-riho -Hexofuranosid)uronic mentioning

confidence: 99%

“…was added to a soh. of (3S)-3-[(1'S)-l'-amino-3'-methylhutyl]-3,4-dihydro-8-hydroxy-lH-2-henzopyran-1-one [5] ((-)-2; 140 mg, 0.5 mmol) in anh. CH,CI, (1.8 ml) and DMF (0.6 ml) containing anh.…”

Section: ((And)-19)) 916 Mg (80%)mentioning

confidence: 99%

Total Synthesis of the Gastroprotective Substance AI‐77‐B and of Analogues

Durgant¹,

Vogel²

1993

Helvetica Chimica Acta

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The Diels-Alder adducts 8 of furan to I-cyanovinyl acetate were converted into (methyl 3-chloro-5-0-(3-chlorohenzoyl)-2,3-dideoxy-cc -DL-arahino -hexofuranosid)uronic acid ((&)-Ma) and into (methyl 3-azido-5-0 -(3-chlorobenzoyl)-2,3-dideoxy-a -DL-riho -hexofuranosid)uronic acid ((+)-4la). These compounds were condensed to (3S)-3-[(1'S)-1'-amino-3'-methylbutyl]-3,4-dihydro-8-hydroxyisoconinarin hydrochloride ((-)-2); the resulting mixtures of diastereoisomeric amides were transformed and separated to give the gastroprotective substance AI-77-B ((-)-1) and analogues.

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“…Because of its intriguing biological properties, there has been significant interest in the synthesis and structural mo-ated anti-aldol reaction with trichlorobutyraldehyde, a novel homopropargylaldehyde equivalent. [15,16] We have recently reported a stereoselective route to AI-77-B in which four of the five stereogenic centres were set by asymmetric synthesis. Condensation of the dihydroisocoumarin and hydroxy amino acid moieties and subsequent removal of the protecting groups furnished optically active AI-77-B.…”

Section: Introductionmentioning

confidence: 99%

Asymmetric Total Synthesis of the Gastroprotective Microbial Agent AI‐77‐B

2003

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An enantioselective total synthesis of the pseudopeptide microbial agent AI‐77‐B, which has shown potent antiulcerogenic properties, is described. The synthesis is convergent and involves the assembly of a dihydroisocoumarin fragment and a hydroxy amino acid. The dihydroisocoumarin derivative was synthesised by means of a Diels−Alder reaction between 1‐methoxy‐1,3‐cyclohexadiene and an alkynyl ester derivative as the dienophile. The alkynyl ester was obtained stereoselectively by two different synthetic routes: (1) A stereoselective allylation of leucinal, and (2) a titanium enolate‐mediated anti‐aldol reaction with trichlorobutyraldehyde, a novel homopropargylaldehyde equivalent. The stereocentres of the hydroxy amino acid moiety were generated through a titanium enolate‐mediated syn‐aldol reaction, Curtius rearrangement, and application of Dondoni's aldehyde homologation. Condensation of the dihydroisocoumarin and hydroxy amino acid moieties and subsequent removal of the protecting groups furnished optically active AI‐77‐B. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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Efficient total synthesis of AI-77-B, A gastroprotective substance from bacillus pumilus AI-77

Cited by 85 publications

References 26 publications

Expression of a functional fungal polyketide synthase in the bacterium Streptomyces coelicolor A3(2)

Expression of a functional fungal polyketide synthase in the bacterium Streptomyces coelicolor A3(2)

Total Synthesis of the Gastroprotective Substance AI‐77‐B and of Analogues

Asymmetric Total Synthesis of the Gastroprotective Microbial Agent AI‐77‐B

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