Total synthesis of (−)-depyranoversicolamide BElectronic supplementary information (ESI) available: Experimental procedures and characterization data for new compounds. See DOI: 10.1039/c5cc05877e

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 ind...

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Bibliographic Details
Main Authors Qin, Wen-Fang, Xiao, T, Zhang, D, Deng, Lin-Feng, Wang, Y, Qin, Y
Format Journal Article
LanguageEnglish
Published 27.10.2015
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Summary: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. Asymmetric total synthesis of (−)-depyranoversicolamide B ( 12 ) is described from easily prepared chiral pyrroloindoline 21 . Key steps in the synthesis are reductive ring opening of the pyrrolo ring in 21 and stereoselective intramolecular Diels-Alder reaction of 18 .
Bibliography:Electronic supplementary information (ESI) available: Experimental procedures and characterization data for new compounds. See DOI
10.1039/c5cc05877e
ISSN:1359-7345
1364-548X
DOI:10.1039/c5cc05877e