Applications of type II Anion Relay Chemistry (ARC). Part 1 : Diversity-Oriented Synthesis of polysubstituted piperidine analogues via Type II ARC. Part 2 : A highly convergent synthesis of (-)-secu'amamine a exploiting Type II ARC. Part 3 : Facile access to diverse carbobicyclic systems via Type II ARC.

Format:

Book

Thesis/Dissertation

Author/Creator:

Han, Heeoon.

Contributor:

University of Pennsylvania. Chemistry.

Language:

English

Subjects (All):

Chemistry, Organic.

0490.

Local Subjects:

0490.

Physical Description:

340 pages

Contained In:

Dissertation Abstracts International 75-01B(E).

System Details:

Mode of access: World Wide Web.

text file

Summary:

In this dissertation, three successful applications of Type II Anion Relay Chemistry (ARC), a versatile multi-component union tactic, are described.

Part 1: An effective, general protocol for the Diversity- Oriented Synthesis (DOS) of 2,4,6-trisubstituted piperidine congeners has been designed and validated. The successful strategy entails a modular approach to all possible stereoisomers of a selected piperidine scaffold, exploiting Type II Anion Relay Chemistry (ARC), followed in turn by intramolecular SN2 cyclization, chemoselective removal of the dithiane moieties and carbonyl reductions.

Part 2: A highly convergent synthesis of (-)-secu'amamine A has been achieved by exploiting a highly efficient Type II Anion Relay Chemistry (ARC) tactic to provide the full carbon and nitrogen skeleton with requisite functionalities in a single-flask.

Part 3: One-step access to diverse carbobicycles utilizing Type II ARC envolving Aldol-Brook Rearrangement-Cyclization Cascade reaction was proposed and validated.

Notes:

Source: Dissertation Abstracts International, Volume: 75-01(E), Section: B.

Adviser: Amos B. Smith, III.

Thesis (Ph.D.)--University of Pennsylvania, 2013.

Local Notes:

School code: 0175.

ISBN:

9781303396151

Access Restriction:

Restricted for use by site license.