Frontiers in Natural Product Chemistry

Author(s): Suchada Chantrapromma, Hoong-Kun Fun, Surat Laphookhieo, Saroj Cheenpracha and Chatchanok Karalai

DOI: 10.2174/978160805212710501010099

Determination of Absolute Configuration of Natural Products by X-ray Diffraction: A Novel Approach of Incorporating Heavy-Atom-Containing Solvent Molecules into the Single Crystals and Refinement of Flack Parameter

Pp: 99-106 (8)

Buy Chapters

* (Excluding Mailing and Handling)

  • * (Excluding Mailing and Handling)

Abstract

SHS investigation development is considered from the geographical and historical viewpoint. 3 stages are described. Within Stage 1 the work was carried out in the Department of the Institute of Chemical Physics in Chernogolovka where the scientific discovery had been made. At Stage 2 the interest to SHS arose in different cities and towns of the former USSR. Within Stage 3 SHS entered the international scene. Now SHS processes and products are being studied in more than 50 countries.

Abstract

In this study, the method of determining the absolute configurations of 14b-hydroxy-3β-O-(L-thevetosyl)-5β-card-20(22)-enolide (I) which was isolated from the air-dried fruits of Cerbera odollam and 3α-feruloyl-taraxerol (II) which was isolated from the air-dried fruits of Bruguiera cylindrica will be presented. The novel method [1] of incorporating heavy-atom-containing solvent molecules into the single crystal structure of the compounds and refinement of the Flack parameter [2] was used to find the absolute configurations of these natural products. Compounds (I) has a cardenolide skeleton whereas compound (II) has a taraxerol skeleton. The present X-ray study shows the absolute L-form of (I) and the absolute α-form of (II). We have clearly demonstrated for the first time a novel approach which is an extremely useful and easy method to determine the absolute stereochemistry of natural products by X-ray diffraction. The importance of determining the absolute stereochemistry of natural products is emphasised in this work.

Recommended Chapters

We recommend

Favorable 70-S: Investigation Branching Arrow

Authors:Bentham Science Books