Asymmetric total synthesis of erythromycin. 3. Total synthesis of erythromycin

Rb, Woodward; Logusch, Eugene W.; Nambiar, K. P.; Sakan, Kunio; Ward, D. E.; Au-Yeung, B. W.; Balaram, Padmanabhan

doi:10.1021/ja00401a051

Cited by 202 publications

(63 citation statements)

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“…A fairly low stability of the previously studied thioimidates was the major reason that the use of benzothiazolyl, [15] pyridin-2-yl, [16][17][18] pyrimidin-2-yl, [16,19] imidazolin-2-yl, [16] and 1'-phenyl-1H-tetrazolyl [20] glycosides in oligosaccharide synthesis was limited. Our…”

Section: =Nrmentioning

confidence: 99%

S‐Thiazolinyl (STaz) Glycosides as Versatile Building Blocks for Convergent Selective, Chemoselective, and Orthogonal Oligosaccharide Synthesis

Pornsuriyasak

Demchenko

2006

Chemistry A European J

103

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In the aim of developing new procedures for efficient oligosaccharide assembly, a range of S-thiazolinyl (STaz) glycosides have been synthesized. These novel derivatives were evaluated against a variety of reaction conditions and were shown to be capable of being chemoselectively activated in the armed-disarmed fashion. Moreover, the S-thiazolinyl moiety exhibited a remarkable propensity for selective activation over other common leaving groups. Conversely, a variety of leaving groups could be selectively activated over the STaz moiety, which, in turn, allowed STaz/S-ethyl and STaz/S-phenyl orthogonal approaches. To demonstrate versatility of novel STaz derivatives, a number of oligosaccharide targets have been synthesized in a convergent selective, orthogonal, and chemoselective fashion.

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Section: =Nrmentioning

confidence: 99%

S‐Thiazolinyl (STaz) Glycosides as Versatile Building Blocks for Convergent Selective, Chemoselective, and Orthogonal Oligosaccharide Synthesis

Pornsuriyasak

Demchenko

2006

Chemistry A European J

103

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“…[223] Das Interesse der Synthesechemiker wurde umgehend geweckt durch die komplexe Struktur von 6 mit ihren 10 Stereozentren und den ungewöhnlichen -an den 14-gliedrigen Lactonring gebunden -Kohlenhydraten l-Cladinose und d-Desosamin. Die Totalsynthesen von Erythronolid A und Erythromycin durch die Gruppen um Corey (1979) [224] und Woodward (1981) [225] sind Meilensteine der Synthesechemie.…”

Section: Makrolid-und Ketolid-antibiotikaunclassified

Antibakterielle Naturstoffe in der medizinischen Chemie – Exodus oder Renaissance?

et al. 2006

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Zur Entwicklung von Medikamenten müssen die Strukturvorlagen aus der Natur oft durch Semisynthese oder Totalsynthese verbessert werden (chemische Post‐Evolution). Der Weg vom Naturstoff zum Arzneimittel ist mühsam aber lohnenswert. Die grundlegenden Typen der chemischen Naturstoffmodifikation – Dekoration, Substitution und Abbau – werden hier besprochen, und das biologische, chemische und sozioökonomische Umfeld antibakterieller Forschung wird betrachtet. Naturstoffe waren und bleiben die ergiebigste Leitstrukturquelle für vermarktete Antiinfektiva, und obwohl viele lange bekannte Klassen nie grundlegend erforscht worden sind, erlahmen die industrielle wie die akademische Forschung auf diesem Gebiet – die “altmodischen” Naturstoffe scheinen nicht mehr ins Bild der modernen Wirkstoff‐Forschung zu passen, ihre Handhabung ist aufwändig und erfordert oft nichtstandardisierte Prozesse und längere Bearbeitungszeiten. Eine Neubetrachtung von Naturstoffen mit Methoden der modernen Chemie und Biologie (Reversed Genomics) könnte ihre Renaissance in der Arzneimittelforschung einleiten.

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“…The catalogue of Woodwards achievements in the total synthesis of natural products include quinine [(AE )-homomeroquinene (17) or (+)-quinotoxine, 1944], patulin (1950), [94] cholesterol and cortisone (1952), [95] lanosterol (1954), [96] lysergic acid and strychnine (1954), [97] reserpine (1958), [98] ellipticine (1959), [99] chlorophyll a (1960), [100] tetracycline (1962), [101] colchicine (1965), [102] cephalosporin C (1966), [103] prostaglandin F 2a (1973), [104] and his paramount achievement: the synthesis of vitamin B 12 (1973, with A. Eschenmoser). [105] The total synthesis of erythromycin A was published in 1981, [106] after his death. Woodwards genius contributed to the deduction of the structures of penicillin (1945), [107] patulin (1949), [108] strychnine (1947), [109] oxytetracycline (1952), [110] carbomycin (magnamycin, 1953), [111] cevine (1954), [112] gliotoxin (1958), [113] calycanthine (1960), [114] oleandomycin (1960), [115] streptonigrin (1963), [116] and tetrodotoxin (1964), [117] as well as others.…”

Section: Methodsmentioning

confidence: 99%

The Quest for Quinine: Those Who Won the Battles and Those Who Won the War

2005

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For a long time, the synthesis of quinine constituted an elusive target. In 2004, which marked the 60th anniversary of the publication of the approach used by Woodward and Doering to synthesize quinine, two new stereocontrolled total syntheses of the natural product were accomplished. Together with the well-publicized first stereocontrolled total synthesis of quinine by Stork in 2001, these publications evidence the revival of interest of organic chemists in the synthesis of this compound, once considered a miracle drug. The recently disclosed syntheses of quinine also testify in a remarkable manner the huge progress made by organic synthesis during the last three decades since the first series of partially controlled syntheses of quinine by the group of Uskokovic. Following an account of the historical importance of quinine as an antimalarial drug and a brief description of the experiments which contributed to its isolation and structural elucidation, the first reconstructions of quinine and the total syntheses of the natural product are discussed.

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Asymmetric total synthesis of erythromycin. 3. Total synthesis of erythromycin

Cited by 202 publications

References 1 publication

S‐Thiazolinyl (STaz) Glycosides as Versatile Building Blocks for Convergent Selective, Chemoselective, and Orthogonal Oligosaccharide Synthesis

S‐Thiazolinyl (STaz) Glycosides as Versatile Building Blocks for Convergent Selective, Chemoselective, and Orthogonal Oligosaccharide Synthesis

Antibakterielle Naturstoffe in der medizinischen Chemie – Exodus oder Renaissance?

The Quest for Quinine: Those Who Won the Battles and Those Who Won the War

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