The potential of Hagemann’s ester as a building block in the synthesis of complex and biologically active natural products is the topic of this report. Hagemann’s ester chemical transformations allowed the development of diverse and creative applications frequently entailing a wide range of new and modern chemistry. The collected material, covering the development of its chemistry from the very beginning up to the present time, has been organized in sections where the papers listed are discussed in chronological order. Sections 1 and 2 are dedicated to a short introduction and to a description of the different preparations of Hagemann’s ester. The alkylation of the vinylogous beta-keto ester system, the most common operation on the starting ester, has been discussed in detail in Section 3. Synthetic applications involving chemical modifications of the ester functionality, namely removal, preservation and elaboration, have been considered in Sections 4–6, while syntheses featuring Hagemann’s ester fragmentation into linear carbon chains are collected in Section 7. Finally, Section 8 has been dedicated to the preparation and synthetic applications of optically active Hagemann’s ester derivatives. For the sake of clarity, the carbon-atom fragments of the different synthetic targets coming from Hagemann’s ester or its analogues are marked in red.
Hagemann's ester: a timeless building block for natural product synthesis
POLLINI, Gian Piero;BENETTI, Simonetta;DE RISI, Carmela;ZANIRATO, Vinicio
2010
Abstract
The potential of Hagemann’s ester as a building block in the synthesis of complex and biologically active natural products is the topic of this report. Hagemann’s ester chemical transformations allowed the development of diverse and creative applications frequently entailing a wide range of new and modern chemistry. The collected material, covering the development of its chemistry from the very beginning up to the present time, has been organized in sections where the papers listed are discussed in chronological order. Sections 1 and 2 are dedicated to a short introduction and to a description of the different preparations of Hagemann’s ester. The alkylation of the vinylogous beta-keto ester system, the most common operation on the starting ester, has been discussed in detail in Section 3. Synthetic applications involving chemical modifications of the ester functionality, namely removal, preservation and elaboration, have been considered in Sections 4–6, while syntheses featuring Hagemann’s ester fragmentation into linear carbon chains are collected in Section 7. Finally, Section 8 has been dedicated to the preparation and synthetic applications of optically active Hagemann’s ester derivatives. For the sake of clarity, the carbon-atom fragments of the different synthetic targets coming from Hagemann’s ester or its analogues are marked in red.I documenti in SFERA sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
