Amino acids Maillard-type condensation

The Brimble group reported the synthesis of acortatarin A 20 in 2012. As in the first synthesis of acortatarin A 20 by Sudhakar et al. a traditional acid-catalyzed dehydrative spiroketalization was used as one of the final steps. However, instead of performing the previously used disconnection between CIO and N9, as several other groups have reporteda Maillard-type condensation reaction between amino alcohol 50 and the sugar surrogate 51 would be used to give 49. The amine 50 would come from D-mannitol and 51 would be prepared from furfuryl alcohol on a gram scale (Scheme l )" ... 

The polymeric material from the plain caramel is generated from the condensation reactions of the aldehydes and ketones formed by heating the sugar with bases or acids. The ammonia caramel is formed in a Maillard type reaction [2] where carbonyl compounds react with amino groups or ammonia. This type of compound will be further presented in Sections 11.2 and 11.3. Sulfite caramel is also a Maillard type polymer. However, as hydrogen sulfites form stable adducts with aldehydes and ketones, the sulfite caramels include in their structure sulfite groups. 

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