Total synthesis of (−)-isatisine A via a biomimetic benzilic acid rearrangement. Issue 22 (3rd June 2015)
- Record Type:
- Journal Article
- Title:
- Total synthesis of (−)-isatisine A via a biomimetic benzilic acid rearrangement. Issue 22 (3rd June 2015)
- Main Title:
- Total synthesis of (−)-isatisine A via a biomimetic benzilic acid rearrangement
- Authors:
- Xiao, Mingxing
Wu, Wei
Wei, Lin
Jin, Xiaojie
Yao, Xiaojun
Xie, Zhixiang - Abstract:
- Abstract: 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. Graphical abstract:
- Is Part Of:
- Tetrahedron. Volume 71:Issue 22(2015)
- Journal:
- Tetrahedron
- Issue:
- Volume 71:Issue 22(2015)
- Issue Display:
- Volume 71, Issue 22 (2015)
- Year:
- 2015
- Volume:
- 71
- Issue:
- 22
- Issue Sort Value:
- 2015-0071-0022-0000
- Page Start:
- 3705
- Page End:
- 3714
- Publication Date:
- 2015-06-03
- Subjects:
- Biomimetic synthesis -- Isatisine A -- Benzilic acid rearrangement -- Anti-HIV
Chemistry, Organic -- Periodicals
547.005 - Journal URLs:
- http://www.elsevier.com/journals ↗
- DOI:
- 10.1016/j.tet.2014.09.028 ↗
- Languages:
- English
- ISSNs:
- 0040-4020
- Deposit Type:
- Legaldeposit
- View Content:
- Available online (eLD content is only available in our Reading Rooms) ↗
- Physical Locations:
- British Library DSC - 8796.850000
British Library DSC - BLDSS-3PM
British Library STI - ELD Digital store - Ingest File:
- 1011.xml