Cyclophanes, transannular inverse electron demand Diels-Alder reactions and a formal total synthesis of (±)-strychnine

Li, Jiang (2002) Cyclophanes, transannular inverse electron demand Diels-Alder reactions and a formal total synthesis of (±)-strychnine. Doctoral (PhD) thesis, Memorial University of Newfoundland.

[img] [English] PDF (Migrated (PDF/A Conversion) from original format: (application/pdf)) - Accepted Version
Available under License - The author retains copyright ownership and moral rights in this thesis. Neither the thesis nor substantial extracts from it may be printed or otherwise reproduced without the author's permission.

Download (47Mb)
  • [img] [English] PDF - Accepted Version
    Available under License - The author retains copyright ownership and moral rights in this thesis. Neither the thesis nor substantial extracts from it may be printed or otherwise reproduced without the author's permission.
    (Original Version)

Abstract

Chapter 1 overviews the relationship between cyclophanes and natural product synthesis. The ultimate objective of the present study is to seek a potential employment of cyclophane intermediates en route to complex natural product skeleta. Chapter 2 describes the synthesis of 2,11-dithia[3.3]metacyclophanes bearing sulfur-containing groups at the 6 and 15 positions. Chapter 3 details the synthesis of some (1,3)indolophanes and the analysis of their conformational behavior. Further study of the hydroboration/Suzuki-Miyaura strategy, as an expedient entry into [3.3]cyclophanes, is also reported. Chapter 4 presents a synthesis of an indolopyridazinophane, relying on the hydroboration/Suzuki-Miyaura strategy. The subsequent transannular inverse electron demand Diels-Alder (IEDDA) reaction of the resulting cyclophane has established efficient access to a highly compact pentacyclic indoloid skeleton. Chapter 5 demonstrates a formal total synthesis of (±)-strychnine, one of the most complex natural products for its size, by preparing Rawal's key pentacyclic intermediate via the cyclophane approach.

Item Type: Thesis (Doctoral (PhD))
URI: http://research.library.mun.ca/id/eprint/1213
Item ID: 1213
Additional Information: Includes bibliographical references
Department(s): Science, Faculty of > Chemistry
Date: 2002
Date Type: Submission
Library of Congress Subject Heading: Organic compounds--Synthesis; Cyclophanes--Synthesis; Strychnine--Synthesis; Diels-Alder reaction

Actions (login required)

View Item View Item

Downloads

Downloads per month over the past year

View more statistics