Novel synthesis of prostaglandin F2.alpha.

Woodward, R. B.; Gosteli, J.; Ernest, I.; Friary, R.; Westler, G; Raman, H.; Sitrin, Robert D.; Suter, C; Whitesell, J W

doi:10.1021/ja00801a066

Cited by 77 publications

(22 citation statements)

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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.…”

Section: Methodsmentioning

confidence: 99%

“…Like an artists personal signature, Woodward recurrently used this feature with increasing mastery in the subsequent and more demanding syntheses of reserpine, vitamin B 12 , and erythromycin A. [98,104,105] Woodward ingeniously visualized that the basic homomeroquinene skeleton could be accessed from an isoquinoline (Scheme 9). Synthetic routes and protocols for the preparation of such compounds were available from the beginning of the century, [131] but truly innovative research cannot be planned to the last detail.…”

Section: Methodsmentioning

confidence: 99%

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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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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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

2005

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“…Verschiedene Strukturen von beispielloser Komplexität wurden angesichts seiner Genialität und Findigkeit eine nach der anderen durch Synthese bezwungen. Die folgenden Verbindungen (siehe auch Abbildung 3) stehen für seine spektakulärsten Syntheseleistungen: Chinin (1944), [22] Patulin (1950), [23] Cholesterin und Cortison (1951), [24] Lanosterin (1954), [25] Lysergsäure (1954), [26] Strychnin (1954), [27] Reserpin (1958), [28] Chlorophyll a (1960), [29] Colchicin (1965), [286] Cephalosporin C (1966), [30] Prostaglandin F 2a (1973), [31] Vitamin B 12 (zusammen mit Eschenmoser 1973) [32] und Erythromycin A (1981) [33] . Einige dieser Totalsynthesen werden in Abschnitt 3.5 kurz vorgestellt.…”

Section: Die ¾Ra Vor Dem Zweiten Weltkriegunclassified

Der Stand der Totalsynthese zu Beginn des 21. Jahrhunderts

Nicolaou¹,

et al. 2000

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Ein neues Jahrtausend hat begonnen – Grund genug, sich die Frage zu stellen, welchen Stand die Totalsynthese von Naturstoffen erreicht hat. Dieser Aufsatz möchte eine Antwort geben, indem er die Entwicklung dieser chemischen Disziplin, die Aspekte von exakter Wissenschaft und schöner Kunst in sich vereint, von Anbeginn bis in die heutige Zeit beschreibt; es wird geschildert, wie viel wir in der Wissenschaft der Totalsynthese schon erreicht haben, aber auch, dass dieses Forschungsgebiet den Kinderschuhen gerade erst entschlüpft.

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“…Thus, the mixture of2a and 2b was subjected to ammonolysis with 28% aqueous ammonia solution in a sealed tube ml20°C for 3 h to give a mixture ofthe~-amino alcohol 3a and 3b. 6 Without purification, reaction of the mixture with nitrous acid furnished the ring-expanded bicy-clo{3.2.l]octenone4 (56% yield) accompanied with a small amount of isomer 5 (7% yield). Reaction ofbicydo{3.2.I]octenone 4 with lithium aluminum hydride, methyllithium, vinylmagnesium bromide, isopropenylmagnesium bromide or phenylmagnesium bromide gave the corresponding exo-alcohols 6a-e in moderate to good yields (Scheme II).…”

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confidence: 99%