Author:
Graeff Daniel P.,Sims Noah J.,Savage Quentin R.,Jackson Richard K.,Jackson Amy C.,Lawson Danielle M.,Wixom Madelyn R.,Wood John L.
Abstract
Abstract
This chapter presents the procedure for the preparation of N‐Boc‐3‐methylpyrrole via Anionic Rearrangement. The pyrrole moiety is found in a wide range of chemical compounds including, but not limited to, natural products, therapeutics, polymers, and dyes. Moreover, these privileged heterocycles can participate in a number of useful carbon‐carbon bond‐forming reactions, thereby rendering them valuable synthetic intermediates. The chapter details the development of a two‐step synthesis of N‐Boc‐3‐ methylpyrrole. The synthesis proceeds through a Diels–Alder reaction between isoprene and the nitroso dienophile derived via oxidation with phenyliodine diacetate. The synthesis employs inexpensive and non‐toxic reagents and is anticipated to expand the use of this privileged heterocycle through broadened access.
Reference12 articles.
1. Contact information: John L. Wood (ORCID 0000‐0002‐9066‐5588) Department of Chemistry and Biochemistry Baylor University Waco TX 76706 (e‐mail:John_L_Wood@Baylor.edu). The authors gratefully acknowledge financial support from Baylor University the Welch Foundation (Chair AA‐006) the Cancer Prevention and Research Institute of Texas (CPRIT R1309) NIGMS‐NIH (R01GM136759) and NSF (CHE‐1764240).
2. Recent progress in the total synthesis of pyrrole-containing natural products (2011–2020)
3. Synthesis of N-perfluoroalkyl-3,4-disubstituted pyrroles by rhodium-catalyzed transannulation of N-fluoroalkyl-1,2,3-triazoles with terminal alkynes
4. The scope of the chemical reactions that pyrroles participate in is far too broad for this communication. The review listed served as a guide to develop a formal [4+2] cycloaddition with 3‐methylpyrrole in our synthetic efforts towards Longeracemine (see reference 4). Chen Z.; Trudell M. L. Chemistry of 7‐Azabicyclo[2.2.1]hepta‐2 5‐dienes 7‐Azabicyclo[2.2.1]hept‐2‐enes and 7‐Azabicyclo[2.2.1]heptanes.Chem. Rev.1996 96 1179–1194 (doi.org/10.1021.cr9500388).
5. Synthetic studies toward longeracemine: a SmI2-mediated spirocyclization and rearrangement cascade to construct the 2-azabicyclo[2.2.1]heptane framework