A versatile total synthesis of α-D-purpurosaminides C

Schwesinger, Berit; Schwesinger, Reinhard; Prinzbach, Horst

doi:10.1016/s0040-4039(01)90091-7

Cited by 8 publications

(1 citation statement)

References 14 publications

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“…The organic phase was dried (MgSO,) and evaporated. 3.20 mmol) and NaBH, (1 .OO g,26.00 mmol) at 0 "C within 5 h (total conversion, TLC). The reaction mixture was neutralized with acetic acid, filtered (Celite), and evaporated and the residue was diluted with water; the dried (MgSO,) organic phase was evaporated to give a syrup (620 mg, -65%, the COCF, group was not totally lost).…”

Section: Methyl 2346-tetradeoxy-2-hydroxyimino-6-( Tr$uoroacetyl-[ ( ...mentioning

confidence: 99%

Total syntheses of enantiomerically pure D- and L-glycosyl donors as components of sannamycin-type aminoglycoside antibiotics

Ludin¹,

Schwesinger²,

Schwesinger³

et al. 1994

J. Chem. Soc., Perkin Trans. 1

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Section: Methyl 2346-tetradeoxy-2-hydroxyimino-6-( Tr$uoroacetyl-[ ( ...mentioning

confidence: 99%

Total syntheses of enantiomerically pure D- and L-glycosyl donors as components of sannamycin-type aminoglycoside antibiotics

Ludin¹,

Schwesinger²,

Schwesinger³

et al. 1994

J. Chem. Soc., Perkin Trans. 1

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Aminoglycoside Antibiotics — Modified, Enantiopure Sannamine‐ and Sporamine‐Type Glycosyl Acceptors

et al. 1994

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Along an established scheme, 1,2 :3,4-dianhydrodeoxy-epiinositol (3) -readily available from benzene -has been applied to expeditious syntheses of suitably protected, fluorinated, and epimerized aminoglycoside building blocks related to sannamine (rac-lla, rac-l6a, rac-l8a, rac-31a) and sporamine (rac-2la, rac-23a, rac-26a, rac-34a). By separation of diastereomers formed with (+)-(1-phenylethy1)amine (14c/ 14'c; 16d16'c) or with (-)-camphanic acid (14e/14'e) and by enzymatic hydrolysis (rac-14b) access is gained to enantiopure glycosyl acceptors.The transformation of benzene into highly functionalized cyclohexanes is a matter of topical interest [']. To us, the development of highly expeditious routes to the triepoxycyclohexanes 1 [trianhydro-cis(allo)-inositols, cis(tmns)-benzene trioxides], diepoxycyclohexanes 2 [dianhydro-cis(epi, muco)-inositols], and 3 [dianhydro-deoxy-cis(epi)-inositols] has induced a systematic study of their applicability to the synthesis of aminocyclitols, which function in various forms as building blocks of aminoglycoside With a selection of enantiopure aminocyclitol-type glycosyl acceptors now at and with the parallel elaboration of eficient routes to a considerable number of enantiopure purpurosamine-type glycosyl donors ['], combinations nearly at will in the construction of antibiotic-type glycosides have become possible. In the following paper[lO] a glycosylation study directed toward sannamycin-analogous glycosides with natural and non-natural configurations will be presented. Given the impact which fluorination or epimerization in the aglycon part of aminoglycoside antibiotics can have upon antibacterial activity and toxicity ["] [e. g. fluorinated kanamycins['*], (epi) sporaricin~['~I], we became interested in extending Scheme 1 to the preparation of glycosyl acceptors of type E and F, in which the 4a-OCH3 group of the [*I As in preceding publications, cyclohexane nomenclature is used throughout this paper (antibiotics numbering is given in parentheses).

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