Total synthesis of (−)-neplanocin A

Lim, Mu-Ill; Márquez, Víctor E.

doi:10.1016/s0040-4039(00)94140-6

Cited by 64 publications

(15 citation statements)

References 11 publications

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“…The chemical syntheses of (37-41) and the 3-deazaneplanocins have been reported (123)(124)(125)(126). Compound (37), which is converted to its 5 -triphosphate, has potent antitumor and antiviral activities (127)(128)(129).…”

Section: Neplanocinsmentioning

confidence: 99%

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Nucleosides and Nucleotides

Suhadolnik¹,

Reichenbach²

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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The naturally occurring nucleoside and nucleotide antibiotics exist as either the C ‐ or N ‐glycosides. They include ezomycin A 1 (C 26 H 38 N 8 O 15 S), ezomycin B 1 (C 26 H 39 N 7 O 17 S), ezomycin C 1 (C 26 H 37 N 7 O 16 S), ezomycin A 2 (C 19 H 26 N 6 O 12 ), ezomycin B 2 (C 19 H 25 N 5 O 13 ), ezomycin C 2 (C 19 H 25 N 5 O 13 ), showdomycin (C 9 H 11 NO 6 ), isoshowdomycin (C 9 H 11 NO 6 ), maleimycin (C 7 H 7 NO 3 ), oxazinomycin (C 9 H 11 NO 7 ), pyrazomycin (pyrazofurin) (C 9 H 13 N 3 O 6 ), formycin (C 10 H 13 N 5 O 4 ), formycin B (C 10 H 12 N 4 O 5 ), oxoformycin B (C 10 H 12 N 4 O 6 ). These antibiotics contain a variety of purine and pyrimidine rings. The naturally occurring nucleoside/nucleotide antibiotics, which have been isolated from bacteria, fungi, blue‐green algae, and marine sponges, have proven to be useful biochemical probes in eucaryotic, procaryotic, viral, fungal, and plant systems. The purine nucleosides inhibit protein synthesis, RNA and DNA synthesis, and methyltransferases; they have antimycoplasmal, antiviral, hypotensive, antifungal, antimycobacterial, and antitumor activities and induce sporulation. The pyrimidine nucleosides inhibit protein synthesis, virus replication, RNA and DNA synthesis, and cAMP phosphodiesterase. The imidazole nucleosides inhibit nucleic acid synthesis. The diazepin nucleosides inhibit adenosine deaminase (ADA). The indole nucleosides inhibit bacteria, yeast, fungi, and viruses. The N ‐nucleotide antibiotics include agrocin 84 (C 21 H 34 N 6 O 16 P 2 ), thuringiensin (C 22 H 30 N 5 O 19 P), phosmidosine (C 16 H 24 N 7 O 8 P), fosfadecin (C 13 H 19 N 5 O 10 P 2 ), and fosfocytocin (C 12 H 20 N 4 O 13 P 2 ). Thuringiensin, produced by B. thuringiensis , is a β‐exotoxin that exerts its toxic action on insects and mammals through the inhibition of RNA polymerases. Phosmidosine inhibits pore formation of Botrytis cinerea and Aspergillus niger . Fosfadecin and fosfocytocin inhibit gram‐positive and gram‐negative bacteria.

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Section: Neplanocinsmentioning

confidence: 99%

“…The seven pacidamycins (121)(122)(123)(124)(125)(126)(127), which are isolated from the culture filtrates of S. coeruleorubidus, are structurally similar to the mureidomycins. These seven peptidyl nucleoside antibiotics differ in the terminal amino acid residues (238).…”

Section: Mureidomycins and Pacidamycinsmentioning

confidence: 99%

Nucleosides and Nucleotides

Suhadolnik¹,

Reichenbach²

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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“…D uring the course o f developing new cyclop en tan oid antitum or agents w e becam e in terested in the synthesis of derivatives carrying additional substituents at the p ositions 4 and/or 4a (carbohydrate num bering has b een used through out this w ork for co n v en ien ce) and 1 seem ed to be an id eal starting m aterial since it can be synthe sized in large am ounts by a chiral p o o l approach starting from 5 -0 -b en zy l-2 ,3 -0 -iso p ro p y lid en e-Dribon o-1,4-lactone (2) [11,12]. Chain elongation at the anom eric centre with dim ethyl lithiom ethylp h osp h on ate [8,13] 12 19 Brought to you by | New York University Bobst Library Technical Services Authenticated Download Date | 6/16/15 3:09 PM additional 15 min, then a saturated aqueous so lu tion o f am m onium chloride (25 m l) was added, the reaction m ixture was diluted with diethyl eth er (500 m l), the organic layer was separated, and the aq ueous phase was extracted with ether ( A nalysis for C i8H 2 7 0 8P (402.38) Calcd C 53.73 H 6 .7 6 % , Found C 53.90 H 6 .9 9 % .…”

Section: A H -Cy Clo P En Ta [D ][L]d Io X O L-4 -O N E [ ( -) -L ] mentioning

confidence: 99%

Chiral Pool Synthesis of 4a-Substituted Carbocyclic Cyclopentanoid Nucleoside Precursors, I

Csük

Dörr

Kühn

et al. 1999

Zeitschrift Für Naturforschung B

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A suitable protected D-ribono-1,4-lactone derivative has been used for the straightforward chiral pool synthesis of cyclopentanoid nucleoside precursors. Thus, epoxidation followed by deoxygenation or regioselective ring opening led to nucleoside precursors modified at the positions C(4), C(4a) and C(4,4a) as well as side-chain modified derivatives. The structures of the key intermediates were determined by X-ray analyses.

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“…This amine was further elaborated into (-)-neplanocin as well as into the corresponding uracil and cytosine carbocyclics. 18,86 In the nitrone approach the masked amino group of the carbocyclic amine was incorporated in the starting material. ( ?…”

Section: A Syntheses Of Neplanocinmentioning

confidence: 99%