Document Detail


A Synthetic Approach to Diverse 3-Acyltetramic Acids via O- to C-Acyl Rearrangement and Application to the Total Synthesis of Penicillenol Series.
MedLine Citation:
PMID:  22510093     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
For the efficient approach to medicinally important alpha-branched 3-acyltetramic acids, the key reaction of O- to C- acyl rearrangement using alpha-amino acids-derived 4-O-acyltetramic acids was extensively examined in the presence of various metal salts. Use of CaCl2 or NaI dramatically changed the results in the reaction efficiency and rapidly brought about the desired alpha-branched 3-acyltetramic acids in markedly improved yields. We also discuss an epimerization at C5 stereocenter under the rearrangement conditions as well as the tolerance for structural variation at C3 and C5. In addition to the preceding success in the total synthesis of new cytotoxic tetramic acid, penicillenol A1, this methodology could be also applied to the first total synthesis of penicillenol A2.
Authors:
Tetsuya Sengoku; Yuta Nagae; Yasuaki Ujihara; Masaki Takahashi; Hidemi Yoda
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-4-17
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  -     ISSN:  1520-6904     ISO Abbreviation:  -     Publication Date:  2012 Apr 
Date Detail:
Created Date:  2012-4-18     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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