Download Alkaloid Synthesis (Topics in Current Chemistry) by Hans-Joachim Knölker PDF

By Hans-Joachim Knölker

Lycopodium Alkaloids: Isolation and uneven Synthesis, by means of Mariko Kitajima and Hiromitsu Takayama.- Synthesis of Morphine Alkaloids and Derivatives, through Uwe Rinner and Tomas Hudlicky.- Indole Prenylation in Alkaloid Synthesis, through Thomas Lindel, Nils Marsch and Santosh Kumar Adla.- Marine Pyrroloiminoquinone Alkaloids, by way of Yasuyuki Kita and Hiromichi Fujioka.- man made reviews on Amaryllidaceae and different Terrestrially Derived Alkaloids, by means of Martin G. Banwell, Nadia Yuqian Gao, Brett D. Schwartz and Lorenzo V. White.- Synthesis of Pyrrole and Carbazole Alkaloids, via Ingmar Bauer and Hans-Joachim Knölker.-

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H2, HOAc, HCHO HO 79 % MeO O NMe O HO 5 steps see refs. 55, 60 36 % O 25 O NMe dihydrocodeinone (34) Scheme 3 Rice’s biomimetic synthesis of morphine NMe HO morphine (1) Synthesis of Morphine Alkaloids and Derivatives 43 of formaldehyde and dihydrocodeinone (34) was isolated. The conversion of this material to morphine has been described before [55, 60] and the preparation of dihydrocodeinone (34) constituted the formal synthesis of codeine and/or morphine. 3 Recent Syntheses of Morphine and/or Codeine This section summarizes all syntheses of morphine and codeine published since the last major review in this area was published in 2005 [18].

An exception to this statement are the yields reported in the synthesis of Rice [16], which was performed on a multigram scale. 2 Early Syntheses of Morphine The following section highlights two milestone achievements in morphine synthesis. In 1952, Gates published the first total synthesis of the title alkaloid [1, 2] and was thus able to prove the structure of morphine proposed by Robinson in 1925 to be correct [57]. In addition, both enantiomers of morphine can be accessed following the published route as Gates performed a resolution of an advanced intermediate (see Scheme 2, compound 20).

42 Recent Syntheses of Morphine and/or Codeine . . . . . . . . . . . . . . . . . . . . . . 1 Fukuyama (2006) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2 Hudlicky (2007) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3 Iorga and Guillou (2008) . . .

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