Dissertation Information for Chutian ShuNAME:
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SCHOOL: ADVISORS: COMMITTEE MEMBERS: MPACT Status: Fully Complete Title: The utilization of stoichiometric organomolybdenum complexes for the syntheses of alkaloids Abstract: A novel synthesis of (-)-indolizidine 209B was developed using stoichiometric organomolybdenum complexes. The key steps in the synthesis include an enzymatic resolution of racemic allylic alcohol to provide the corresponding allylic acetate in enantiomerically pure form, a selective methoxide the 2,3,6-trisubstituted dihydropyridinyl complexes, and a regio-, stereo-, and enantiocontrolled demetalation to give the requisite tetrahydropyridine key intermediate. Further demetalation studies showed that 2,3,6-cis-trisubstituted piperidines could also be prepared by carefully choosing the demetalation the pyranyl and dihydropyridinyl complexes was rationalized by a novel stereoelectronic effect based on X-ray crystallography studies of the dimethoxy pyranyl complexes with and without a 3-substituent. complexes without a 3-substituent was achieved using a chiral carbamate as was determined by a total synthesis of (-)-dihydropinidine, and the synthetic potential of this novel desymmetrization method was shown by a total synthesis of (-)-andrachcinidine. The bicyclic core of pumiliotoxin C was prepared using a tandem reaction sequence of lithium-halogen exchange and in situ intrarmolecular nucleophilic addition from an easily prepared 3-pyridone complex. Further studies should lead to an efficient synthesis of (-)-pumiliotoxin C. |
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