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Studies on the Reductive Transannular Rearrangement of α-Amino Cyclic Ketones:Novel Strategies Toward the Azacyclic Core Skeleton Construction of Several Alkaloids

Author: ZhangJian
Tutor: LiWeiDong
School: Lanzhou University
Course: Organic Chemistry
Keywords: α-Amino cyclic ketone Clemmensen-Clemo-Prelog-Leonard reductiverearrangement Alkaloids Total synthesis Lycopodine
CLC: O621.259.3
Type: PhD thesis
Year: 2013
Downloads: 32
Quote: 0
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Abstract


This thesis aims at the study of Clemmensen-Clemo-Prelog-Leonard reductive transannular rearrangement of a-amino cyclic ketones and the construction of the azacyclic skeletons of several typical alkaloids, i.e. Stenine, Aspidospermidine and Lycopodine, which consists of the following three chapters:In Chapter1, general strategic methods to construct the azacyclic skeleton of various alkaloids are summarized. The discovery, further investigation and application of reductive transannular rearrangement of a-amino cyclic ketones are briefly reviewed.In Chapter2, typical synthetic methods for Stenine and Aspidospermidine were reviewed. Experimental studies on novel strategies toward the construction of the core skeletons of alkaloids Stenine and Aspidospermidine via the Clemmensen-Clemo-Prelog-Leonard transannular reductive rearrangement of a-amino cyclic ketones were documented in detail. Thus, the core7-5-6and6-5-6azacyclic skeletons were assembled from their corresponding α-amino cyclic ketone precursors under the classic Clemmensen reduction conditions. Clemmensen-Clemo-Prelog-Leonard Reductive Transannular RearrangementIn Chapter3, the Dieckmann condensation and an efficient Michael-Aldol cascade annulation process were developed for the facile preparation of the novel acetoxylated α-amino cyclic ketone precursors. The6-6-6azacyclic skeleton of Lycopodine and the6-5-6azacyclic skeleton of Aspidospermidine were constructed by the Clemmensen-Clemo-Prelog-Leonard reductive transannular rearrangement of above prepared α-amino cyclic ketones under milder reaction conditions (Zn/HOAc). A formal synthesis of the Lycopodine framework was achieved. Clemmensen-Clemo-Prelog-Leonard Reductive Transannular Rearrangement

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Organic Chemistry general issues > Properties of organic compounds > Chemical properties of organic reactions > Rearrangement reaction
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