Wenkert, Ernest2018-12-182018-12-181983Simmons, Dana Philip. "Indole alkaloid synthesis." (1983) Diss., Rice University. <a href="https://hdl.handle.net/1911/104330">https://hdl.handle.net/1911/104330</a>.https://hdl.handle.net/1911/104330Indole acetic acid and methyl 1,4,5,6-tetrahydronicotinylacetate obtained by hydrogenation of methyl nicotinylacetate were combined in the presence of base to yield methyl 1-(3-indoleacetyl)-1,4,5,6-tetrahydronicotinylacetate in 45% yield. This, upon heating in polyphosphoric acid, yielded in 73% 2-deethyl-5,17-diketo-2,16-dihydrovincadifformine with complete stereospecific formation of all five chiral centers. Reduction of the two keto functions led to 2-deethyl-2,16-dihydrovincadifformine, whereas reduction of the lactam and oxidation of the 2,16 carbon-carbon bond yielded 2-deethyl-16-ketovincadifformine. 16 ketopseudovincadifformine was prepared in the same manner starting from methyl 5-ethyl-nicotinylacetate.77 ppengCopyright is held by the author, unless otherwise indicated. Permission to reuse, publish, or reproduce the work beyond the bounds of fair use or other exemptions to copyright law must be obtained from the copyright holder.ThesisRICE1962reformatted digitalThesis Chem. 1983 Simmons