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A semi‐synthetic analog of the cembranoid sarcophine
Authors:Hesham Fahmy  Jordan K Zjawiony  Sherief Khalifa  Frank R Fronczek
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, C20H32O4, 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) Å, and the mol­ecules are linked into double chains by intermolecular hydrogen bonds with O?O distances of 2.772 (2) and 2.849 (2) Å.
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