부산대학교 도서관

Summary: The evaluations of synthetic approaches to aplydactone and chartellamide A inspired by biosynthetic considerations are described. The first chapter of this thesis provides background information on photochemistry and instances in nature where a photochemical transformation may be incorporated into the biosynthesis of certain natural products. A biogenesis of aplydactone and a related spirocyclic chamigrane sesquiterpene is proposed and a general design for its implementation is discussed in the second chapter. The outcome of a [2+2] cycloaddition/[2+2] cycloreversion strategy for addressing an 8,6-bicycle and the successful implementation of a strained ring fragmentation strategy for generating an alpha-vinyl ketone are also included in the second chapter along with the evaluation of our biosynthetic hypotheses. The final chapter describes (1) photoinduced electron transfer (PET) and some of its applications in organic synthesis, (2) the isolation of the indole-imidazole family of natural products, (3) the synthetic work of other research groups toward their synthesis, (4) the basis of our PET approach to the core structure of chartellamide A, (5) the interesting outcome of our PET investigations, and (6) the genesis of alternative synthetic strategies.