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|Title:||A biomimetic total synthesis of (-)-spirotryprostatin B and related studies||Authors:||Wang, H.
|Issue Date:||28-Jul-2000||Citation:||Wang, H., Ganesan, A. (2000-07-28). A biomimetic total synthesis of (-)-spirotryprostatin B and related studies. Journal of Organic Chemistry 65 (15) : 4685-4693. ScholarBank@NUS Repository. https://doi.org/10.1021/jo000306o||Abstract:||The prenylated natural products spirotryprostatin A and B derived from the Trp-Pro diketopiperazine also feature an oxidative rearrangement of the indole to form a spirooxindole. Synthetically, formation of the oxindole ring was stereoselectively accomplished by reaction of the appropriate indole precursor with N-bromosuccinimide. For optimum results, the oxidation should be carried out prior to diketopiperazine cyclization. In this manner, we have synthesized the tetrahydro- and dihydro- analogues of spirotryprostatin B in four steps from L-tryptophan methyl ester. The dihydro derivative was then converted to spirotryprostatin B by unsaturation of the pyrrolidine ring to a pyrroline, thus unambiguously confirming the structure of the natural product.||Source Title:||Journal of Organic Chemistry||URI:||http://scholarbank.nus.edu.sg/handle/10635/111751||ISSN:||00223263||DOI:||10.1021/jo000306o|
|Appears in Collections:||Staff Publications|
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