Enantioselective Total Synthesis of (+)-Gliocladine C: Convergent Construction of Cyclotryptamine-Fused Polyoxopiperazines and a General Approach for Preparing Epidithiodioxopiperazines from Trioxopiperazine Precursors
作者： John E. DeLorbe , Salman Y. Jabri , Steven M. Mennen , Larry E. Overman , Fang-Li Zhang
DOI: 10.1021/JA201789V
关键词: Total synthesis 、 Chemistry 、 Yield (chemistry) 、 Substituent 、 Stereocenter 、 Isatin 、 Enantioselective synthesis 、 Pyrrolidinones 、 Pyrrolidine 、 Stereochemistry
摘要: A concise second-generation total synthesis of the fungal-derived alkaloid (+)-gliocladin C (11) in 10 steps and 11% overall yield from isatin is reported. In addition, epipolythiodioxopiperazine (ETP) natural product (+)-gliocladine (6) has been prepared six 29% di-(tert-butoxycarbonyl) precursor 11. The 6 constitutes first an ETP containing a hydroxyl substituent adjacent to quaternary carbon stereocenter pyrrolidine ring.
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