ChemInform Abstract: The Boronic Acid Mannich Reaction in Alkaloid Synthesis

ChemInform ◽  
2013 ◽  
Vol 44 (43) ◽  
pp. no-no
Author(s):  
Stephen G. Pyne ◽  
Andrew S. Davis ◽  
Thunwadee Ritthiwigrom ◽  
Christopher W. G. Au ◽  
Kongdech Savaspun ◽  
...  
Keyword(s):  
Mannich Reaction ◽  
Boronic Acid ◽  
Alkaloid Synthesis

scholarly journals The boronic acid Mannich reaction in alkaloid synthesis

2012 ◽  
Vol 85 (6) ◽  
pp. 1215-1225 ◽  
Author(s):  
Stephen G. Pyne ◽  
Andrew S. Davis ◽  
Thunwadee Ritthiwigrom ◽  
Christopher W. G. Au ◽  
Kongdech Savaspun ◽  
...  
Keyword(s):  
Mannich Reaction ◽  
Boronic Acid ◽  
Pyrrolizidine Alkaloids ◽  
Alkaloid Synthesis

Our work on the application of the boronic acid Mannich reaction to the synthesis of pyrrolizidine alkaloids is described.

Construction the A-B bicyclic ring structure of Stemocurtisisne

2020 ◽  
Vol 17 ◽  
Author(s):  
Duc Dau Xuan
Keyword(s):  
Glutamic Acid ◽  
Natural Product ◽  
Mannich Reaction ◽  
Boronic Acid ◽  
Ring Opening ◽  
Ring Structure ◽  
Starting Material ◽  
Epoxide Ring ◽  
Epoxide Ring Opening

: The synthesis of the A-B bicyclic ring structure 3 of the natural product Stemocurtisine is described. The synthesis was accomplished in seven synthetic steps from commercially available L-glutamic acid. The key step involved a borono-Mannich reaction between the hemiaminal 6 and trans-β-styryl boronic acid and trans-β-styrylpotassiumtrifluoroborate to prepare the cis diene 4. Attempts to prepare the A-B-C ring compound 2 via intramolecular epoxide ring opening followed by rearangement under different basic conditions were unsuccessful. Only unreactive starting material was recovered.

scholarly journals Exploiting the borono-Mannich reaction in bioactive alkaloid synthesis

2008 ◽  
Vol 80 (4) ◽  
pp. 751-762 ◽  
Author(s):  
Stephen G. Pyne ◽  
Christopher W. G. Au ◽  
Andrew S. Davis ◽  
Ian R. Morgan ◽  
Thunwadee Ritthiwigrom ◽  
...  
Keyword(s):  
Mannich Reaction ◽  
Amino Alcohols ◽  
Core Structure ◽  
Indolizidine Alkaloids ◽  
Acyliminium Ions ◽  
Alkaloid Synthesis

We have demonstrated that the borono-Mannich reaction is a versatile and efficient reaction for the diastereoselective preparation of chiral 1,2-amino alcohols. These Mannich products are valuable starting materials as shown in this report by the synthesis of bioactive polyhydroxylated pyrrolizidine and indolizidine alkaloids. Initial studies, directed at the more complex Stemona alkaloids and using the borono-Mannich reaction on cyclic N-acyliminium ions, are encouraging, as demonstrated by the synthesis of the pyrido[1,2-a]azepine core structure of stemocurtisinol.

ChemInform Abstract: Utilization of Aminophosphonates in the Petasis Boronic Acid Mannich Reaction.

ChemInform ◽  
2010 ◽  
Vol 41 (19) ◽  
Author(s):  
Michael V. Shevchuk ◽  
Alexander E. Sorochinsky ◽  
Volodymyr P. Khilya ◽  
Vadim D. Romanenko ◽  
Valery P. Kukhar
Keyword(s):  
Mannich Reaction ◽  
Boronic Acid

The Boronic Acid Mannich Reaction

2013 ◽  
pp. 211-498 ◽  
Author(s):  
Stephen G. Pyne ◽  
Minyan Tang
Keyword(s):  
Mannich Reaction ◽  
Boronic Acid
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