Synthesis and Biotransformation of Bicyclic Unsaturated Lactones with Three or Four Methyl Groups.

Katarzyna Wińska,Adrianna Kondas,Wanda Mączka,Gabriela Maciejewska,Radosław Bonikowski,Mirosław Anioł,Małgorzata Grabarczyk

doi:10.3390/molecules22010147

Abstract

The aim of this study was to obtain new unsaturated lactones by chemical synthesis and their microbial transformations using fungal strains. Some of these strains were able to transform unsaturated lactones into different hydroxy or epoxy derivatives. Strains of Syncephalastrum racemosum and Absidia cylindrospora gave products with a hydroxy group introduced into a tertiary carbon, while the Penicillium vermiculatum strain hydroxylated primary carbons. The Syncephalastrum racemosum strain hydroxylated both substrates in an allylic position. Using the Absidia cylindrospora and Penicillium vermiculatum strains led to the obtained epoxylactones. The structures of all lactones were established on the basis of spectroscopic data.

Highlights

Hydroxylactones are a very important group of natural compounds
5bobtained were obtained from a synthesis the corresponding known allylic alcohols
1b were subjected to four-step from synthesis from the corresponding known allylicSubstrates alcohols. 1a

Summary

Introduction

Hydroxylactones are a very important group of natural compounds. Such compounds are often encountered in Nature, mainly in plants and marine organisms. Because lactones occur in natural sources in small amounts, their isolation is hard and expensive. From this it follows that in order to study these biologically active compounds it is necessary to obtain them by means other than isolation from their natural sources. One such method is hydroxylation of synthetically obtained lactones by means of biotransformations. The presence of a double bond in these molecules leads to the introduction of a hydroxy group into the allylic position [11,12,13,14,15,16,17,18]

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Conclusion