First total synthesis of glabramycin B and revision of its relative configuration. Issue 23 (8th June 2017)
- Record Type:
- Journal Article
- Title:
- First total synthesis of glabramycin B and revision of its relative configuration. Issue 23 (8th June 2017)
- Main Title:
- First total synthesis of glabramycin B and revision of its relative configuration
- Authors:
- Yamamoto, Masaoki
Ishigami, Ken
Watanabe, Hidenori - Abstract:
- Abstract: Structural revision of glabramycin B, which is an antibacterial 10-membered lactone isolated from a fermentation broth of Neosartorya glabra, was achieved by enantioselective synthesis of our proposed structure. The correct structure of glabramycin B was presumed on comparison with related compounds, and synthesis of it was succeeded via dianion alkylation, Shiina's lactonization and Stille cross-coupling. By this synthesis, we were able to correct the reported structural misassignment, and to confirm the relative configuration of glabramycin B to be 10 S *, 11 S *, 15 R *, 20 S *. Graphical abstract:
- Is Part Of:
- Tetrahedron. Volume 73:Issue 23(2017)
- Journal:
- Tetrahedron
- Issue:
- Volume 73:Issue 23(2017)
- Issue Display:
- Volume 73, Issue 23 (2017)
- Year:
- 2017
- Volume:
- 73
- Issue:
- 23
- Issue Sort Value:
- 2017-0073-0023-0000
- Page Start:
- 3271
- Page End:
- 3280
- Publication Date:
- 2017-06-08
- Subjects:
- Glabramycin B -- Ten-membered lactone -- Antibiotics -- Determination of the relative configuration -- Sch 642305
Chemistry, Organic -- Periodicals
547.005 - Journal URLs:
- http://www.elsevier.com/journals ↗
- DOI:
- 10.1016/j.tet.2017.04.061 ↗
- 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:
- 2285.xml