3-Hydroxy-ɣ-butyrolactone (3-BHL) is an important target in synthetic organic chemistry. 3-BHL is listed among the top value-added chemicals from biomass and it is considered as a powerful chiral building block for the preparation of natural products, nutraceuticals and blockbuster drugs as Crestor, Lipitor, Zyvox and Zetia. Accordingly, several methods for its preparation have been reported and include chemical synthesis, chemo-enzymatic approaches and biosynthetic routes. However, despite great progresses have been made, more practical, economical and sustainable synthesis are still needed. In this communication we report a novel strategy for the preparation of enantiopure 3-BHL. In particular, we show the set-up and assessment of an integrated flow system that enables the continuous synthesis of 3-BHL from 3-butenoic acid with high purity by means of in-line downstream operations such as extraction, purification, and on-time analysis. Our current efforts in improving the method by the assistance of kinetic enzymatic resolution will be also presented and discussed.
Continuous Flow Synthesis and Enzymatic Resolution of 3-Hydroxy-ɣ-Butyrolactone (3-BHL): A Key Building Block for Synthesis and Drugs
Blasi F;Cerra B;Cossignani L
;Gioiello A
2018
Abstract
3-Hydroxy-ɣ-butyrolactone (3-BHL) is an important target in synthetic organic chemistry. 3-BHL is listed among the top value-added chemicals from biomass and it is considered as a powerful chiral building block for the preparation of natural products, nutraceuticals and blockbuster drugs as Crestor, Lipitor, Zyvox and Zetia. Accordingly, several methods for its preparation have been reported and include chemical synthesis, chemo-enzymatic approaches and biosynthetic routes. However, despite great progresses have been made, more practical, economical and sustainable synthesis are still needed. In this communication we report a novel strategy for the preparation of enantiopure 3-BHL. In particular, we show the set-up and assessment of an integrated flow system that enables the continuous synthesis of 3-BHL from 3-butenoic acid with high purity by means of in-line downstream operations such as extraction, purification, and on-time analysis. Our current efforts in improving the method by the assistance of kinetic enzymatic resolution will be also presented and discussed.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
