2-AZA-[3,3]-Sigmatropic rearrangement and AZA-PRINS cyclization and their applications in total synthesis of (-)-indolizidine-209B and (-)-perhydrohistrionicotoxin

2-AZA-[3,3]-Sigmatropic rearrangement and AZA-PRINS cyclization and their applications in total synthesis of (-)-indolizidine-209B and (-)-perhydrohistrionicotoxin

Two novel C-C bond formation methodologies, i.e. 2-AZA-[3,3]-sigmatropic rerrangement and aza-Prins cyclization, were developed for the synthesis of linear homoallylic hydroxylamines and 2,3,6-trisubstituted piperidines respectively. These two nitrogen-containing compounds are useful building block...

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Bibliographic Details
Main Author: Cheng, Hin Soon
Other Authors: Loh Teck Peng
Format: Theses and Dissertations
Language:English
Published: 2010
Subjects:
DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis
Online Access:https://hdl.handle.net/10356/42458
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Institution: Nanyang Technological University
Language: English
Description
Summary:Two novel C-C bond formation methodologies, i.e. 2-AZA-[3,3]-sigmatropic rerrangement and aza-Prins cyclization, were developed for the synthesis of linear homoallylic hydroxylamines and 2,3,6-trisubstituted piperidines respectively. These two nitrogen-containing compounds are useful building blocks in many natural products. The applications of these methodologies were then demonstrated in the total syntheses of both (-)-indolizidine 209B and (-)-perhydrohistrionicotoxin.

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