Transannular Diels-Alder model studies on the total synthesis of chatancin. The furanophane approach. Part 2 [1]: Macrocyclization and Diels-Alder reaction

摘要

Title investigation of three generations of model substrates targeting chatancin is presented. An unfunctionalized furan affords a reversible transannular Diels-Alder reaction producing only the two TAC-frameworks where the expected one is the kinetic product. A furan 3-COOMe functionalization allows the selective formation of the expected isomer which is still favored even in the presence of a quasi-axial isopropyl group on the furanophane. (C) 1999 Elsevier Science Ltd. All rights reserved. [References: 8]