Chemoenzymatic synthesis of amaryllidaceae alkaloids and their C-1 analogues : symmetry based approach to total synthesis of thebaine

Described herein is the chemoenzymatic total synthesis of several Amaryllidaceae constituents and their unnatural C-I analogues. A new approach to pancratistatin and related compounds will be discussed along with the completed total synthesis of 7 -deoxypancratistatin and trans-dihydrolycoricidine. Evaluation of all new C-l analogues as cancer cell growth inhibitory agents is described. The enzymatic oxidation of dibromobenzenes by Escherichia coli 1M 109 (pDTG60 1) is presented along with conversion of their metabolites to (-)-conduritol E. Investigation into the steric and functional factors governing the enzymatic dihydroxylation of various benzoates by the same organism is also discussed. The synthetic utility of these metabolites is demonstrated through their conversion to pseudo-sugars, aminocyclitols, and complex bicyclic ring systems. The current work on the total synthesis of some morphine alkaloids is also presented. Highlighted will be the synthesis of several model systems related to the efficient total synthesis of thebaine.

Photograph - Emma Osgood Mead, Osgood Woodruff, and Henry C. Woodruff

Black and white photograph, 6 ½ cm x 10 cm, of 2 women and a man. The inscription on the back reads “Emma Osgood Mead (“Blind Aunt Emma”), Osgood Woodruff and Henry C. Woodruff (Mrs. Percy Band’s father was a cousin to this ‘Uncle Henry’).

Marriage Certificate - Hamilton K. Woodruff and Julia C. Cleveland

The marriage certificate of Mr. Hamilton K. Woodruff of St. Catharines and Miss Julia C. Cleveland of Erie, Pennsylvania. This is certificate no. 5221 signed by James C. Wilson. This is accompanied by 2 envelopes; one envelope is from Henry L. Rea, clerk of courts, Erie Pennsylvania to Mr. H. K. Woodruff, the other envelope just says "marriage certificate Mrs. H. K. Woodruff", Nov. 21, 1894.