A semi-synthetic analog of the cembranoid sarcophine.

作者信息

Fahmy Hesham, Zjawiony Jordan K, Khalifa Sherief, Fronczek Frank R

机构信息

Department of Pharmacognosy and National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, University of Mississippi, University, MS 38677-1848, USA.

出版信息

Acta Crystallogr C. 2003 Feb;59(Pt 2):o85-7. doi: 10.1107/s0108270103001288. Epub 2003 Jan 31.

DOI:10.1107/s0108270103001288

PMID:12574663

Abstract

The title molecule, 2(R)-[(1E,3E,7S,8S,11E,13R)-13-hydroxy-4,8,12-trimethyl-7,8-epoxycyclotetradeca-1,3,11-trien-1-yl]propane-1,2-diol, C(20)H(32)O(4), is a semi-synthetic analog of sarcophine, the natural cembranoid of marine origin, isolated from the soft coral Sarcophyton glaucum. The conformation of the 14-membered ring differs substantially from that of sarcophine. The two OH groups of the propane-1,2-diol moiety form an unusual weak intramolecular hydrogen bond with an O...O distance of 2.788 (2) A, and the molecules are linked into double chains by intermolecular hydrogen bonds with O...O distances of 2.772 (2) and 2.849 (2) A.

摘要