Bicyclo[3.3.0]octane-2,6-dione and bicyclo[3.3.0]octa-3,7-diene-2,6-dione

Hagedorn, Alfred A.; Farnum, Donald G.

doi:10.1021/jo00443a035

Cited by 34 publications

(16 citation statements)

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“…Next, we attempted to convert diketone 29 directly into the dienedione 11. [30] For example, treatment of 29 with potassium hexamethyldisilazane (KHMDS) and phenylselenylbromide followed by H 2 O 2 oxidation [31] gave 30 % of an inseparable 1:1:1 mixture of starting material 29, dienedione 11, and the corresponding bicyclo[3.3.0]oct-3-ene-2,6-dione. Enol ether formation with trimethylsilyl triflate (TMSOTf), NEt 3 , [32] and Saegusa oxidation with Pd(OAc) 2 /benzoquinone [33] resulted in a complex mixture containing 41 % of derivative 11, whereas a modified procedure [34] gave no trace of the target compound 11.…”

Section: Resultsmentioning

confidence: 99%

“…1 The spectroscopic data agreed with those in the literature. [30] Dimethyl (3a'R,4R,5R,6a'R)-4'-oxo-4',6a'-dihydro-3a'H-spiro [1,3- b) HCl (25 mL, 1 n) was added to a solution of compound 36 (9.26 g, 41.0 mmol) in THF/MeOH/acetone 6:1:1 (250 mL) and the reaction mixture was stirred for 1 h. After quenching with a satd solution of NaHCO 3 , the mixture was extracted with EtOAc (300 mL). The organic layer was dried (MgSO 4 ) and concentrated.…”

Section: Methyl (2e)-5-[(tert-butoxycarbonyl)amino]pent-2-enoate (13)mentioning

confidence: 99%

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Total Synthesis and NMR Investigations of Cylindramide

Cramer

Buchweitz

Frey

et al. 2006

Chemistry A European J

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Cylindramide (1) was built up from three components: a hydroxyornithine derivative 7, a tetrazolylsulfone 8, and a substituted pentalene subunit 9. Derivative 7 was prepared in a six-step reaction sequence involving the Wittig reaction and a Sharpless asymmetric dihydroxylation starting from N-Boc-3-aminopropanal (12). Tetrazolylsulfone 8 was accessible in four steps from dioxinone 22. The synthesis of the pentalene fragment 9 started from cycloocta-1,5-diene 26, that was converted into enantiopure bicyclo[3.3.0]octanedione 29. The latter was functionalized to give derivative 9. The total synthesis was accomplished by inducing C-C bond formation by Sonogashira coupling of derivatives 9 and 7 followed by olefination with tetrazolylsulfone 8 under Julia-Kocienski conditions, macrocyclization, and subsequent Lacey-Dieckmann condensation to form the tetramic acid unit. As indicated by extensive 1H and 13C NMR spectroscopic investigations (DQF-COSY, ROESY spectra), the stereochemistry of synthetic cylindramide (1) corresponds with that of the naturally occurring product. ROE data were used for molecular modeling of the lowest-energy structures for cylindramide.

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Section: Resultsmentioning

confidence: 99%

Section: Methyl (2e)-5-[(tert-butoxycarbonyl)amino]pent-2-enoate (13)mentioning

confidence: 99%

Total Synthesis and NMR Investigations of Cylindramide

Cramer

Buchweitz

Frey

et al. 2006

Chemistry A European J

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“…Methanobacterium formicicum JF-1, Methanobacterium bryantii MOH, and Methanospirillum hungatei JF were grown in 10-liter batches on a medium modified from Schauer and Ferry (15), consisting of 1.44 g of NH4C1, 1.14 g of K2HPO4, 1.14 g of KH2PO4, 0.5 g of yeast extract (Difco Laboratories, Detroit, Mich.), 0.5 g of tryptone (Difco), 6.0 g of sodium formate, 2.0 g of sodium acetate, 0.01 g of Fe(NH4)SO4, 5.0 g of Na2HCO3, 0.001 g of resazurin, 0.46 g of NaCl, 0.092 g of MgCl2 6H20, 0.26 g of CaCl2 .2H20, 0.25 g of cysteine hydrochloride, and 0.25 g of Na2S 9H20 per liter of water. In addition, vitamin and trace mineral solutions (2) were each added to a final 2% (vol/vol) concentration.…”

Section: Methodsmentioning

confidence: 99%

Structural diversity among methanofurans from different methanogenic bacteria

White

1988

J Bacteriol

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An examination of the methanofurans isolated from a wide range of methanogenic bacteria and from Archaeoglobus fulgidus has revealed at least five chromatographically distinct methanofurans. Bacteria from each major genus of methanogenic bacteria have been found to contain a chemically different methanofuran. The nature of the differences in the methanofurans appears to lie in the modification of the side chain attached to the basic core structure of 4-[N-(-y-L-glutamyl--y-L-glutamyl)-p-(,-aminoethyl)phenoxymethyl]-2-(aminomethyl)furan. This was supported by the structural elucidation of the methanofuran isolated from Methanobrevibacter smithii, designated methanofuran-c, which was the same as the originally characterized methanofuran except for a hydroxy group at the 2 position of the 4,5-dicarboxyoctanedioic acid moiety of the molecule.Methanofuran (Fig. 1) is a recently characterized cofactor in the conversion of CO2 to methane by methanogenic bacteria (9-11). It is involved in the first step of CO2 reduction, where it serves as a C1 carrier at the formyl level of carbon oxidation (7,10 aminomethyl)furan with different attached side chain molecules. This is supported by the structural analysis of the methanofuran from Methanobrevibacter smithii, which shows it to consist of this basic core structure, peptide bonded, via the terminal glutamyl residue, to the C-1 of 2-hydroxy-4,5-dicarboxyoctanedioic acid (2-hydroxyDCO) (Fig. 1). MATERIALS AND METHODSBacterial strains and growth. Methanobacterium formicicum JF-1, Methanobacterium bryantii MOH, and Methanospirillum hungatei JF were grown in 10-liter batches on a medium modified from Schauer and Ferry (15), consisting of 1.44 g of NH4C1, 1.14 g of K2HPO4, 1.14 g of KH2PO4, 0.5 g of yeast extract (Difco Laboratories, Detroit, Mich.), 0.5 g of tryptone (Difco), 6.0 g of sodium formate, 2.0 g of sodium acetate, 0.01 g of Fe(NH4)SO4, 5.0 g of Na2HCO3, 0.001 g of resazurin, 0.46 g of NaCl, 0.092 g of MgCl2 6H20, 0.26 g of CaCl2 .2H20, 0.25 g of cysteine hydrochloride, and 0.25 g of Na2S 9H20 per liter of water. In addition, vitamin and trace mineral solutions (2) were each added to a final 2% (vol/vol) concentration. Methanobrevibacter smithii PS was grown in 3-liter batches on a medium modified from that of Lovley et al. (13), consisting of 0.45 g of K2HPO4, 0.15 g of KH2PO4, 0.12 g of NH4C1, 0.3 g of NaCl, 0.04 g of CaCl2 2H20, 2.5 g of NaHCO3, 0.14 g of MgCl2 6H20, 2.5 g of sodium acetate, 5.0 g of sodium formate, 2.0 g of yeast extract, 2.0 g of tryptone, 0.0001 g of resazurin, 0.5 g of cysteine hydrochloride, and 0.5 g of Na2S 9H20 per liter of water. Also added were antifoam C, 0.0005% (vol/vol); vitamin and trace mineral solutions (2), 1% each (vol/vol); iosbutyric, 2-methylbutyric, isovaleric, and valeric acids, each to a final concentration of 0.0005% (vol/vol); and Tween 80, 0.002% (vol/vol).Methanococcus maripaludis JJ was provided by William B. Whitman, Department of Microbiology, University of Georgia, Athens. The organism was grown by Whitman on a comple...

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“…Bicyclo[3.3.0]octane dione, which has functionality in each cyclopentane ring and is suitable for stereocontrolled assembly of more complex structures, has versatile intermediates, particularly the bicyclo[3.3.0]octane framework (Fig. ).…”

mentioning

confidence: 99%

“…Furthermore, chiral bicyclo [3.3.0]octane derivatives have been used as chiral ligands in catalytic asymmetric reactions, [22][23][24] Therefore, development of an efficient procedure for the enantio-and diastereo-controlled construction of the bicyclo [3.3.0]octane framework is very important because the number of methods (in particular, enantio-and diastereo-controlled methods) is limited. [25][26][27][28][29][30][31][32][33] Bicyclo[3.3.0]octane dione, which has functionality in each cyclopentane ring and is suitable for stereocontrolled assembly of more complex structures, has versatile intermediates, particularly the bicyclo[3.3.0]octane framework 34,35 (Fig. 2).…”

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confidence: 99%

Development of Chiral Building Blocks Having a Bicyclo[3.3.0]Octane Framework Using a Diastereomeric Resolution‐Selective Deprotection

2015

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A protocol is presented for an efficient and practical approach to the synthesis of enantiomerically pure bicyclo[3.3.0]octane derivatives from achiral Cs-symmetric bicyclo[3.3.0]octane-2,8-dione using a diastereomeric resolution-selective deprotection method. This method affords chiral building blocks having bicyclo[3.3.0]octane framework with the same site of diastereotopic carbonyl functional group.

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Bicyclo[3.3.0]octane-2,6-dione and bicyclo[3.3.0]octa-3,7-diene-2,6-dione

Cited by 34 publications

References 0 publications

Total Synthesis and NMR Investigations of Cylindramide

Total Synthesis and NMR Investigations of Cylindramide

Structural diversity among methanofurans from different methanogenic bacteria

Development of Chiral Building Blocks Having a Bicyclo[3.3.0]Octane Framework Using a Diastereomeric Resolution‐Selective Deprotection

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