Skip to main content
eScholarship
Open Access Publications from the University of California

UC San Diego

UC San Diego Electronic Theses and Dissertations bannerUC San Diego

Asymmetric Total Synthesis of Cylindrocyclophanes A and F through Cyclodimerization and a Ramberg-Bäcklund Reaction and Studies Directed Towards the Total Synthesis of CJ-16, 264 /

  • Author(s): Korman, Henry
  • et al.
Abstract

Cylindrocyclophanes A and F are naturally occurring cyclophanes with beautiful molecular architectures and important biological properties that have inspired numerous syntheses. Chapter 1 details the isolation and biological properties of these molecules, our retrosynthetic analysis, and asymmetric total syntheses of these molecules. The highlights of this synthesis includes a "head-to-tail" dimerization reaction and a Ramberg- Bäcklund olefination reaction to generate the [7.7]- paracyclophane found in these molecules. CJ-16,264, UCS1025A, and pyrrolizilactone belong to a unique class of natural products isolated from fungi, each containing a [gamma]-hydroxypyrrolizidinone adjoined to a decalin. Their unique architectures, as well as their amazing biological activities, has inspired several syntheses of UCS1025A. There has been no report, to the best of our knowledge, of a successful synthesis of CJ-16,264 or pyrrolizilactone. Chapter 2 describes the isolation and biological properties of these molecules, our retrosynthetic analysis, the synthesis of (±)-1-epi-CJ-16 ,264 and our significant contributions towards the synthesis CJ-16,264. The highlights of this synthesis include a double exo-selective IMDA (intramolecular Diels- Alder) reaction and a stereoselective Reformatsky-type cross coupling to generate the common scaffold of these molecules

Main Content
Current View