Studies on a Simple Route to a Bicyclic Reserpine Intermediate
- 1 November 1989
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 19 (17) , 2987-2997
- https://doi.org/10.1080/00397918908052692
Abstract
A concise route is described to a Reserpine synthetic intermediate having the features of ring E and an oxygen function for constructing ring D. This involves an unusual α-diketone cleavage, the selective elaboration of the carboxylated ring in 1-naphthoic acids and selective boron halide cleavage of ester and ether groups.Keywords
This publication has 24 references indexed in Scilit:
- General strategies for the synthesis of indole alkaloids. Total synthesis of (.+-.)-reserpine and (.+-.)-.alpha.-yohimbineJournal of the American Chemical Society, 1987
- Stereospecific synthesis of substituted cis-hydrindan-5-one and their regiospecific enolization and functionalization: synthetic intermediates for reserpineJournal of the American Chemical Society, 1984
- General methodology for cis-hydroisoquinoline synthesis: synthesis of reserpineJournal of the American Chemical Society, 1980
- A total synthesis of reserpineJournal of the American Chemical Society, 1979
- A Synthetic Approach to Reserpine and Related CompoundsHETEROCYCLES, 1979
- A new approach to substituted arene oxides. Total synthesis of senepoxide and seneolJournal of the American Chemical Society, 1978
- Synthesis of compounds related to gibberellic acid. III. Analogs of ring A of the gibberellinsThe Journal of Organic Chemistry, 1969
- An Approach to Ring E of Reserpinoid SubstancesThe Journal of Organic Chemistry, 1965
- The total synthesis of reserpineTetrahedron, 1958
- Ueber sauerstoffhaltige Derivate des AcenaphtensEuropean Journal of Organic Chemistry, 1893