scholarly journals 3-Trifluoromethylcephalosporins. I. Total synthesis of tert-butyl (.+-.)-7-amino-3-trifluoromethyl-3-cephem-4-carboxylate.

1980 ◽  
Vol 28 (1) ◽  
pp. 62-69 ◽  
Author(s):  
TAIICHIRO WATANABE ◽  
YOICHI KAWANO ◽  
TERUO TANAKA ◽  
TOSHIHIKO HASHIMOTO ◽  
TETSUO MIYADERA
Keyword(s):  
Synlett ◽  
2020 ◽  
Vol 32 (01) ◽  
pp. 45-50
Author(s):  
Udo Nubbemeyer ◽  
Analuisa Nava ◽  
Lukas Trippe ◽  
Andrea Frank ◽  
Lars Andernach ◽  
...  

AbstractStarting from methyl cycloheptatrienyl-1-carboxylate, 6-acylation was successfully achieved employing glutaryl chloride in the presence of AlCl3 under controlled reaction conditions to furnish keto carboxylic acid product. After protection of this keto carboxylic acid as tert-butyl ester, reagent-controlled enantioselective reductions delivered configuration-defined methyl-6-hydroxylalkyl cycloheptatriene-1-carboxylates with up to 80% ee. Whereas simple NaBH4 reduction of the keto carboxylic acid and subsequent lactonization afforded a methyl-6-tetrahydropyranonyl cycloheptatriene-1-carboxylate. Resolution using chiral HPLC delivered the product enantiomers with up to >99% ee Finally, ECD analyses enabled structure elucidation. The products are used as key intermediates in enantioselective 6,11-methylene-lipoxin B4 syntheses.


1986 ◽  
Vol 64 (4) ◽  
pp. 658-666 ◽  
Author(s):  
Hsing-Jang Liu ◽  
Hla Wynn

The first total synthesis of α-costal (1) in racemic form has been achieved in an unequivocal manner whereby the structure previously assigned to the natural aldehyde is confirmed. A salient feature of the synthesis is the use of S-tert-butyl cyanothiolacetate to facilitate the introduction of the labile acrolein unit.


1987 ◽  
Vol 52 (24) ◽  
pp. 5452-5457 ◽  
Author(s):  
Luca Banfi ◽  
Walter Cabri ◽  
Giovanni Poli ◽  
Donatella Potenza ◽  
Carlo Scolastico

1978 ◽  
Vol 56 (1) ◽  
pp. 62-70 ◽  
Author(s):  
James P. Kutney ◽  
John Balsevich ◽  
Gordon H. Bokelman ◽  
Toshihiko Hibino ◽  
Toshio Honda ◽  
...  

Studies involving selective functionalization of the indole unit in a number of bisindole alkaloids and related synthetic derivatives are described. These investigations include such reagents as tert-butyl hydroperoxide, which provides an efficient procedure for epoxidation of olefinic linkages, mercuric acetate, osmium tetroxide, and iodine under basic conditions and oxygenation under acidic conditions. Efficient syntheses of leurosine (8) and various novel vinblastine derivatives are developed.


ChemInform ◽  
1988 ◽  
Vol 19 (17) ◽  
Author(s):  
L. BANFI ◽  
W. CABRI ◽  
G. POLI ◽  
D. POTENZA ◽  
C. SCOLASTICO

2017 ◽  
Vol 58 (29) ◽  
pp. 2835-2837 ◽  
Author(s):  
Yunpeng Zou ◽  
Shouguo Zhang ◽  
Xiaoxue Wen ◽  
Gang wang ◽  
Yunbo sun ◽  
...  
Keyword(s):  

1993 ◽  
Vol 48 (7) ◽  
pp. 1000-1008 ◽  
Author(s):  
Peter Link ◽  
Wolfgang Voelter

As part of our total synthesis of thymosin β4 an optimized synthesis of the C-terminal part of thymosin β4 is described. Side chain functional residues of the tridecapeptide are masked by tert-butyl and the α-amino residues are protected by Z groups. The fully protected peptide derivative was obtained by WSCI/HOBt coupling of three fragments representing the segments [31-35], [36-37] and [38-43].


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