10.1002/asia.201000458
The research focuses on the total synthesis of (±)-morphine, an analgesic that is essential for controlling cancer pain. The study addresses the challenges of synthesizing morphine due to its complex five-ring skeleton and quaternary carbon center. The researchers developed an efficient synthetic route that overcomes previous shortcomings, such as cumbersome installation of the aminoethyl moiety and inefficient functionalization of the C ring. Key reactants include 2-cyclohexen-1-one, which undergoes a series of transformations including enzymatic resolution, Suzuki-Miyaura coupling, intramolecular aldol reaction, and intramolecular 1,6-addition to construct the morphinane core. The synthesis also employed Mitsunobu and Heck reactions. Analyses used to characterize the intermediates and final products included 1H and 13C NMR, high-resolution mass spectrometry (HRMS), infrared (IR) spectroscopy, and specific rotation measurements. The overall yield of the synthesis was 5%, and the longest linear sequence from the starting material consisted of 17 steps.
10.1016/j.tetlet.2007.11.037
The research centers on the formal synthesis of (-)-morphine, commencing from D-glucal. The core experimental procedures involve the preparation of the C-ring using Ferrier's carbocyclization reaction and the stereoselective generation of adjacent tertiary and quaternary carbons in the C-ring through a cascade Claisen rearrangement. The synthesis sequence includes a Suzuki-Miyaura coupling to form an intermediate, followed by the crucial cascade Claisen rearrangement to construct the adjacent tertiary and quaternary carbons, which are integral to the morphine structure. Subsequently, an intramolecular Friedel-Crafts type reaction is employed to build the ABCE-phenanthrofuran skeleton, and the introduction of a tosylamide function precedes a reductive cyclization to yield (-)-dihydroisocodeine, a known synthetic intermediate for (-)-morphine. Various analytical techniques, such as nuclear magnetic resonance (NMR), infrared (IR) spectroscopy, mass spectrometry (MS), and elemental analysis, are utilized to characterize the newly synthesized compounds. The reactants encompass a range of organic acids, alkali metals, organic boronic acids, and D-glucal derivatives.
10.1016/S0040-4020(01)92063-0
The research aimed to explore chemical transformations of Pummerer's Ketone to synthesize molecules with simplified morphine structures, potentially leading to the development of analgesics with improved properties. The study focused on converting Pummerer's Ketone into compounds with nitrogen-bearing functions at the C-4 position, thereby approximating the morphine skeleton. The study concluded that certain conditions, such as the use of cerous chloride with NaBH4, could influence the selectivity of the reduction process. Additionally, the addition of N,N-diethylaminopropyne provided a successful route to introduce a nitrogen atom into the molecule, leading to the formation of an amide.
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