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Total synthesis of (-)-depyranoversicolamide B
Wen-Fang Qin1, T Xiao1, D Zhang2
1The Innovative Drug Research Centre, and School of Chemistry and Chemical Engineering, Chongqing University, Chongqing 401331, P. R. China.
Chemical Communications (Cambridge, England)
|September 23, 2015
Abstract:
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.