A sample of deoxosarcophine (2) was converted into sarcophine (L) by autoxidation. TWO reactions are described that will enable the enantiomers of deoxosarcophine to be interrelated.
The structure of sarcophine (l.), a cembranoid from Sarcophyton glaucum, was determined by single crystal X-ray diffraction analysis 1 and the absolute . configuration assigned from CD data.' The same soft coral was later shown to contain several related cembranoids, including two isomeric dihydrofurans having the spectral characteristics of stereoisomers of deoxosarcophine (2). Kashman3 was unable to fully characterize these compounds but presented evidence to show that the dihydrofurans were epimers at C-2. Co114 has described an isomer of deoxosarcophine (2) from Sarcophyton ehrenbergi while Tursch' has reported, without details, an isomer of compound 3 from S. trocheliophorum.
Selected physical data are compared in Table 1. We wish to report the correlation of our sample of deoxosarcophine (3 with sarcophine (&). The soft coral Sarcophyton sp. was collected by SCUBA (-5m) from the leeward side of Canton Island (2'5O'S, 171ยฐ40'w). Chromatography of dichloromethane soluble material on Florisil gave deoxosarcophine (z), m.p. 73'C, as the major metabolite (1.1% dry weight). Comparison of the spectral data' with those published by Kashman3 convinced us that we had an isomer of deoxosar-