ABSTRACT

Zhao, X. and Yang, S., 2018. The asymmetric synthesis of furanoseterterpene from marine natural products. In: Liu, Z.L. and Mi, C. (eds.), Advances in Sustainable Port and Ocean Engineering. Journal of Coastal Research, Special Issue No. 83, pp. 386–391. Coconut Creek (Florida), ISSN 0749-0208.

In this paper, the asymmetric synthesis of furanoseterterpene from marine natural products is studied. In the stereo selective synthesis of 16-deacetoxy-scalarafuran, (+) -scalarolid and the analogues of both, scalareol is as starting material and by eight steps reaction, methyl ent-isocopalate is synthetized; in the synthesis of sesterstatins 4/5 and scalarafuran, methyl ent-isocopalate is as the intermediate, to complete the stereoinversion hydroxyl. The key intermediate, III-25, is obtained by Wittig reaction, and the halogenated furan ring is introduced. The intramolecular reductive Heck reaction is as the key step, to get the natural product sesterstatins 4/5 and scalarafuran; in the synthesis of sesterterpene compounds with furan ring, compound II-16 is as the substrate, and the intermediate IV12 and IV13 can be obtained by four steps reaction; the epoxy compounds are obtained by double bond epoxidation. Experiments show that this method is very versatile and greatly improves the development accuracy of marine products.

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