Abstract
Xestenone is a marine norditerpenoid found in the northeastern Pacific sponge Xestospongia vanilla. The relative configuration of C-3 and C-7 in xestenone was determined by NOESY spectral analysis. However the relative configuration of C-12 and the absolute configuration of this compound were not determined. The authors have now achieved the total synthesis of xestenone using their developed one-pot synthesis of cyclopentane derivatives employing allyl phenyl sulfone and an epoxy iodide as a key step. The relative and absolute configurations of xestenone were thus successfully determined by this synthesis.
Highlights
The norditerpenoid xestenone (Figure 1) was first isolated from the marine sponge Xestospongia vanilla in 1988 [1]
The authors planned to synthesize both xestenone and 12-epi-xestenone, since the relative configuration at C-12 of xestenone was unknown at the onset (Scheme 2)
For the right hand fragment of xestenone, aldehyde B would be synthesized from cyclopentane D through various chemical functionalizations
Summary
The norditerpenoid xestenone (Figure 1) was first isolated from the marine sponge Xestospongia vanilla in 1988 [1]. No biological activity has been reported for xestenone, various bioactive compounds that have been isolated from several Xestospongia sponges [2]. The authors recently reported a stereocontrolled one-pot synthesis of cyclopentane derivatives possessing a quaternary carbon, which involved: 1) reaction of an anion derived from allyl phenyl sulfone with epoxy iodide I to give epoxysulfone II; 2) in situ deprotonation of II to generate an epoxysulfone anion III and 3) intramolecular cyclization to give cyclopentane derivative IV This one-pot synthesis of cyclopentane derivatives has been applied to the total synthesis of xestenone, and in this paper the authors wish to report on the successful total synthesis of xestenone and its complete structural determination.
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