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• W2028855357 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." @default.
• W2028855357 created "2016-06-24" @default.
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• W2028855357 date "2000-06-23" @default.
• W2028855357 modified "2023-10-16" @default.
• W2028855357 title "A Biomimetic Total Synthesis of (−)-Spirotryprostatin B and Related Studies" @default.
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• W2028855357 doi "https://doi.org/10.1021/jo000306o" @default.
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