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Part I, The stereoselective synthesis of cannabinoids ; Part II, The total synthesis of sarcophytol A and its analogs

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Item Summary

Title: Part I, The stereoselective synthesis of cannabinoids ; Part II, The total synthesis of sarcophytol A and its analogs
Authors: Zou, Xianglong
Keywords: Cannabinoids -- Synthesis
Sarcophyton
Organic compounds -- Synthesis
Issue Date: 1995
Abstract: 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.
Description: Thesis (Ph. D.)--University of Hawaii at Manoa, 1995.
Includes bibliographical references (leaves 124-127).
Microfiche.
xi, 127 leaves, bound ill. 29 cm
URI/DOI: http://hdl.handle.net/10125/9527
Rights: All UHM dissertations and theses are protected by copyright. They may be viewed from this source for any purpose, but reproduction or distribution in any format is prohibited without written permission from the copyright owner.
Appears in Collections:Ph.D. - Chemistry



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