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Total Synthesis and Absolute Stereochemistry of Seragakinone A


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  • 20 セラガキノンAの全合成(口頭発表の部)


Serakakinone A (1), an antifungal and antibacterial compound, was produced by an unidentified marine fungus symbiotic to rhodophyta Ceratodictyon spongiosum collected at Seragaki beach, Okinawa. The intriguing structure of 1 features a densely oxygenated pentacyclic structure with angular prenylation, as determined by extensive spectroscopic studies and single-crystal X-ray analysis, although the absolute configuration remained unassigned. Three major challenges in planning a symthetic route are: (1) the construction of the pentacyclic framework, (2) the stereoselective introduction of a prenyl unit into the sterically hindered angular position, and (3) the regio- and stereo-controlled installation of multiple oxygen functionalities. In this talk, we will present the first asymmetric total synthesis of (-)-seragakinone A. Noteworthy features of the synthesis include: (1) the benzoin-forming reactions worked well at two cyclization stages, including one catalytic enantioselective reaction, (2) the pinacol-type rearrangement was effective for installing tghe angular prenyl substituent. The synthetic material was identical in all respects to the natural sample, except for the sign of optical rotation, thereby allowing the assignment of the synthetic material as the antipode of the natural product.


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