A semi-synthetic analog of the cembranoid sarcophine

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

doi:10.1107/s0108270103001288

A semi-synthetic analog of the cembranoid sarcophine

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

Authors

Hesham Fahmy¹, Jordan K Zjawiony, Sherief Khalifa, Frank R Fronczek

Affiliation

¹ 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.

PMID: 12574663
DOI: 10.1107/s0108270103001288

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

4-Butyrolactone / analogs & derivatives*
4-Butyrolactone / chemical synthesis
4-Butyrolactone / chemistry*
Animals
Anthozoa / chemistry*
Crystallography, X-Ray
Hydrogen Bonding
Models, Molecular

Substances

sarcophine
4-Butyrolactone