Starting from easily prepared (R)-C3-isoprenylated pyrroloindoline, the C3-isoprenylated indolyl diketopiperazine is prepared by an efficient reductive opening of the pyrrolo ring, and undergoes biomimetic Diels-Alder reaction to generate an anti-adduct as a sole stereoisomer. Oxidation of the indoline moiety to oxindole completes the synthesis of (-)-depyranoversicolamide B.
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Total synthesis of (-)-depyranoversicolamide B.
Chem Commun (Camb)
November 2015
Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, West China School of Pharmacy, and State Key Laboratory of Biotherapy, Sichuan University, Chengdu 610041, P. R. China.
Starting from easily prepared (R)-C3-isoprenylated pyrroloindoline, the C3-isoprenylated indolyl diketopiperazine is prepared by an efficient reductive opening of the pyrrolo ring, and undergoes biomimetic Diels-Alder reaction to generate an anti-adduct as a sole stereoisomer. Oxidation of the indoline moiety to oxindole completes the synthesis of (-)-depyranoversicolamide B.
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