Part I, The stereoselective synthesis of cannabinoids ; Part II, The total synthesis of sarcophytol A and its analogs
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1995
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University of Hawaii at Manoa
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Part I: The stereoselective total synthesis of each of the two diastereomeric C6-hydroxyhexahydrocannabinols is described. The extension of isopropenyl to hydroxymethyl was accomplished by the use of an ene reaction with formaldehyde in the presence of methylaluminum bis(2,6-diphenylphenoxide). Stereochemistry of the two final products was controlled by an intramolecular mercuration. Biological testing showed that the analogs exhibit different degrees of binding to the CB1 cannabinoid receptor. Part II: The total synthesis of a dienone precursor of sarcophytol A is described. The conversion of dienone to sarcophytol A has been reported. Hence, this is the formal total synthesis of sarcophytol A. Interesting features of this synthesis include an alkynylation of an allylic halide, macrocyclization, and C-alkylation of a 1,3-diketone with isopropyl iodide. Selective reduction of diketone to dienone was accomplished with DIBAL. It is noteworthy that conversion of sulfoxide directly to the corresponding enone did not succeed through a Pummerer rearrangement. Attempted conversion of sulfone to dienone in the target molecule was not successful and eliminated product was obtained. A synthesis of canventol is also described. Biological testing has shown that canventol is a more potent antitumor promotor than sarcophytol A even though canventol is structurally simpler.
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Cannabinoids--Synthesis, Sarcophyton, Organic compounds--Synthesis
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Theses for the degree of Doctor of Philosophy (University of Hawaii at Manoa). Chemistry; no. 3294
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