The complete structure of the triterpene arborinol

✍ Scribed by Olga Kennard; L. Riva di Sanseverino; H. Vorbrűggen; Carl Djerassi

• Publisher: Elsevier Science
• Year: 1965
• Tongue: French
• Weight: 194 KB
• Volume: 6
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)89324-2

✦ Synopsis

Partial structure I has recently been assigned' on the basis of various physical measurements and chemical reactions to the triterpene arborinol isolated from the leaves of Glycosmis arborea (fain. Rutaceae). Particularly noteworthy from a biogenetic standpoint was the unusual C/D stereochemistry, which had not been encountered hitherto among pentacyclic triterpenes. Insufficient material was available to settle the nature of rings D and E, although II ana III were considered to be likely candidates. The structure of arborinol has now been determined, through a three-dimensional X-ray diffraction study of 2a-bromo-arborinone. The particular derivative chosen afforded an analysis of the structure, without recourse to chemical assumptions other than the existence of discrete atoms in the molecule. The results indicate unequivocally the structure of 2wbromo-arborinone as (IV). Previous chemical studies2 relating to rings A, B, C and the trans configuration of the methyl * External Stdff, Medical Research Council.