Sarcophine, a new epoxy cembranolide from marine origin

J. Bernstein, U. Shmeuli, E. Zadock, Y. Kashman, I. Néeman

Research output: Contribution to journalArticlepeer-review

115 Scopus citations

Abstract

From the soft bodied coral Sarcophytum glaucum a crystalline compound-sarcophine (1), which is believed to be one of the repellents protecting the coral against predators, was isolated. The functional groups of 1 have been deduced from detailed NMR study and the whole molecular structure has been determined by a single-crystal 3-dimensional X-ray diffraction study proceeding from direct methods. The compound crystallizes in orthorhombic crystals, space group P212121, and there are four molecules in each unit cell of dimensions a = 12·429(3), b = 13·766(3) and c = 10·750(1). The structure was found to be a new epoxy cembranolide. The mass spectrum and CD of 1 and several simple derivatives as well as the conformation of 1 in solution are discussed.

Original languageEnglish
Pages (from-to)2817-2824
Number of pages8
JournalTetrahedron
Volume30
Issue number16
DOIs
StatePublished - 1 Jan 1974

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Sarcophine, a new epoxy cembranolide from marine origin'. Together they form a unique fingerprint.

Cite this