A semi-synthetic analog of the cembranoid sarcophine.
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.
Fahmy
Hesham
H
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.
Zjawiony
Jordan K
JK
Khalifa
Sherief
S
Fronczek
Frank R
FR
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*; D000818:Animals; D037421:Anthozoa / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D008958:Models, Molecular
C014804:sarcophine; D015107:4-Butyrolactone