Total synthesis of (−)-isatisine A via a biomimetic benzilic acid rearrangement

The biomimetic total synthesis of potential anti-HIV (−)-isatisine A, a novel alkaloid with an unprecedented fused tetracyclic skeleton, was accomplished in eight steps from indole and known 4,6-O-isopropylidene-protected glucal. The synthetic strategy was inspired primarily by the proposed biogenet...

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Bibliographic Details
Published in:Tetrahedron 2015-06, Vol.71 (22), p.3705-3714
Main Authors: Xiao, Mingxing, Wu, Wei, Wei, Lin, Jin, Xiaojie, Yao, Xiaojun, Xie, Zhixiang
Format: Article
Language:English
Subjects:
Anti-HIV
Benzilic acid rearrangement
Biomimetic synthesis
Isatisine A
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Summary:The biomimetic total synthesis of potential anti-HIV (−)-isatisine A, a novel alkaloid with an unprecedented fused tetracyclic skeleton, was accomplished in eight steps from indole and known 4,6-O-isopropylidene-protected glucal. The synthetic strategy was inspired primarily by the proposed biogenetic hypothesis that indole C-furanoside would be derived from indole C-glucoside via a ring contractive benzilic acid rearrangement. The biogenetic hypothesis was enabled by model studies: the O-glucoside was converted to O-furanoside via a benzilic acid rearrangement. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2014.09.028