Efforts towards the Total Synthesis of Azaspiracid-3

Bibliographic Details
Main Author: Zhang, Zhigao
Language:English
Published: The Ohio State University / OhioLINK 2013
Subjects:
Online Access:http://rave.ohiolink.edu/etdc/view?acc_num=osu1366108671
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spelling ndltd-OhioLink-oai-etd.ohiolink.edu-osu13661086712021-08-03T05:22:06Z Efforts towards the Total Synthesis of Azaspiracid-3 Zhang, Zhigao Chemistry Azaspiracid, a structurally complex marine toxin isolated from the mussel Mytilus edulis in Killary Harbor, Ireland, represents a new class of marine metabolites unrelated to any previous known agent of diarrhetic shellfish posioning. As such, the natural product has spurred considerable interest among organic community. The thesis details the study towards the total synthesis of azaspiracid-3.The C1-C21 domain and C22-C40 domain have been synthesized, which aims to assemble the molecule through Yamaguchi esterification. The ABCD domain involved an efficient NHK coupling reaction between C1-C12 segment and C13-C22 segment. The trioxadispiroketal skeleton was constructed under the influence of acid catalysis. The EFGHI domain highlighted a chelate controlled Mukaiyama aldol reaction to produce C22-C40 linear precursor, and a DIHMA process to assemble the bridged ketal. With the recognition of bridged ketal and spiroaminal functionality in the FGHI domain, the gold-catalysis to achieve these moieties has been proposed. A novel gold-catalyzed spiroaminal formation has been systemically developed. The gold-catalyzed ketallization was then successfully implemented to construct the bridged ketal, while an inevitable elimination could not deliver the desired spiroaminal under gold conditions. A NHK reaction to couple the C1-C21 and C22-C40 domains has also been proposed. The revised C22-C40 domain was achieved with a similar synthetic route. 2013-07-24 English text The Ohio State University / OhioLINK http://rave.ohiolink.edu/etdc/view?acc_num=osu1366108671 http://rave.ohiolink.edu/etdc/view?acc_num=osu1366108671 unrestricted This thesis or dissertation is protected by copyright: all rights reserved. It may not be copied or redistributed beyond the terms of applicable copyright laws.
collection NDLTD
language English
sources NDLTD
topic Chemistry
spellingShingle Chemistry
Zhang, Zhigao
Efforts towards the Total Synthesis of Azaspiracid-3
author Zhang, Zhigao
author_facet Zhang, Zhigao
author_sort Zhang, Zhigao
title Efforts towards the Total Synthesis of Azaspiracid-3
title_short Efforts towards the Total Synthesis of Azaspiracid-3
title_full Efforts towards the Total Synthesis of Azaspiracid-3
title_fullStr Efforts towards the Total Synthesis of Azaspiracid-3
title_full_unstemmed Efforts towards the Total Synthesis of Azaspiracid-3
title_sort efforts towards the total synthesis of azaspiracid-3
publisher The Ohio State University / OhioLINK
publishDate 2013
url http://rave.ohiolink.edu/etdc/view?acc_num=osu1366108671
work_keys_str_mv AT zhangzhigao effortstowardsthetotalsynthesisofazaspiracid3
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