Synthesis of (4S,5S)-4,5-dihydroxy-4,5-O-isopropylidene-2-cyclopenten-1-one from D-ribose.

Ohrui, Hiroshi; Konno, Masao; Meguro, Hiroshi

doi:10.1271/bbb1961.51.625

Cited by 8 publications

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“…The utility of bacterial dioxygenation of aromatic compounds for the subsequent chemical synthesis of chiral cyclopentenes has been demonstrated by Hudlicky et al (21), who used the dihydrodiol formed from toluene, (1S,2R)-1,2-dihydroxy-3-methylcyclohexa-3,5-diene, for the preparation of 3(S)-and 3(R)-methylcyclopent-1-ene-1-carboxaldehydes and (4S,8S)-6,6-dimethyl-5,7dioxabicyclo[3.3.0]oct-2-en-1-one. The latter compound has been obtained in several different multistep syntheses (8,24,31) and has been recognized as a valuable synthon for a number of biologically active cyclopentane derivatives ( Fig. 1).…”

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confidence: 99%

Biotransformation of 6,6-Dimethylfulvene by Pseudomonas putida RE213

Eaton¹,

Selifonov²

1996

Appl Environ Microbiol

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The biotransformation of 6,6-dimethylfulvene [5-(1-methylethylidene)-1,3-cyclopentadiene], a nonaromatic C 5 carbocyclic analog of isopropylbenzene, was examined by using Pseudomonas putida RE213, a Tn5-generated dihydrodiol-accumulating mutant of the isopropylbenzene-degrading strain P. putida RE204. 6,6-Dimethylfulvene was converted to a single chiral product identified as (؉)-(1R,2S)-cis-1,2-dihydroxy-5-(1-methylethylidene)-3-cyclopentene. This isopropylbenzene 2,3-dioxygenase-catalyzed transformation demonstrates the potential of bacterial arene dioxygenases for the direct conversion of cyclopentadienylidene compounds to homochiral C 5 carbocyclic cis-diols for use in enantiocontrolled organic syntheses.

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confidence: 99%

Biotransformation of 6,6-Dimethylfulvene by Pseudomonas putida RE213

Eaton¹,

Selifonov²

1996

Appl Environ Microbiol

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Synthesis and Oxidation of N‐Aminoglyconolactams: A Synthesis of Mannostatin A

Vasella

2004

Helvetica Chimica Acta

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The N-amino-ribono-1,5-lactam 4 was prepared in two high-yielding steps from the known methanesulfonate 2. Oxidation of 4 with t-BuOCl in the presence of 2,6-lutidine afforded the tetrazene 6 (63%). Oxidation with MnO 2 gave the deaminated lactam 7 (40%), which was also obtained, together with the lactone 8, upon oxidation of 4 with PhSeO 2 H. Oxidation with Mn(OAc) 3 /Cu(OAc) 2 provided the lactam 7 as the major and the dimer 9 as the minor product. Oxidation of 4 with 3 equiv. of Pb(OAc) 4 in toluene at room temperature gave two cyclopentanes, viz. the acetoxy epoxide 10 and the diazo ketone 11 in a combined yield of 78%. Oxidation with Pb(OBz) 4 provided 11 and the crystalline benzoyloxy epoxide 12. The crystal structure of 12 was established by X-ray analysis. The N-amino-glyconolactams 41, 46, and 51 were prepared similarly to 4. Their oxidation with Pb(OAc) 4 provided the diazo ketones 56, 57, and 58 as the only isolable products. Oxidation of the N-aminomannono-1,5-lactam 55 with Pb(OAc) 4 in the presence of DMSO gave the sulfoximine 59. Mannostatin A, a strong a-mannosidase inhibitor, was synthesized from the acetoxy epoxide 10 (obtained in 48% from 4) in seven steps and in an overall yield of 45%. . This synthesis renewed our interest in the transformation of carbohydrates into cyclopentanes. Carbohydrates indeed appear to be ideal starting materials for the synthesis of highly functionalized, enantiomerically pure cyclopentanes. The first general method for the transformation of monosaccharides to cyclopentanes is based on a fragmentation and intramolecular 1,3-dipolar cycloaddition [18]

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D

Collins¹

1998

Dictionary of Carbohydrates

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Synthesis of (4S,5S)-4,5-dihydroxy-4,5-O-isopropylidene-2-cyclopenten-1-one from D-ribose.

Cited by 8 publications

References 0 publications

Biotransformation of 6,6-Dimethylfulvene by Pseudomonas putida RE213

Biotransformation of 6,6-Dimethylfulvene by Pseudomonas putida RE213

Synthesis and Oxidation of N‐Aminoglyconolactams: A Synthesis of Mannostatin A

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