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Asymmetric synthesis of (-)-renieramycin T.
- Source :
-
Organic & biomolecular chemistry [Org Biomol Chem] 2016 Aug 14; Vol. 14 (30), pp. 7334-44. Date of Electronic Publication: 2016 Jul 13. - Publication Year :
- 2016
-
Abstract
- (-)-Renieramycin T, an interesting tetrahydroisoquinolinequinone alkaloid with a novel renieramycin-ecteinascidin mixed framework, is synthesized from the known phenol 16 in 22 steps with 6.2% overall yield. In the convergent route, the key cyclocondensation between the isoquinoline moiety 27 and trisubstituted phenylalaninol 14 is achieved with good selectivity to furnish bistetrahydroisoquinoline 29, which permits a rapid construction of the pentacyclic framework having a fully substituted aromatic A ring.
- Subjects :
- Heterocyclic Compounds, 4 or More Rings chemistry
Molecular Conformation
Phenylalanine chemistry
Tetrahydroisoquinolines chemistry
Heterocyclic Compounds, 4 or More Rings chemical synthesis
Isoquinolines chemistry
Phenols chemistry
Phenylalanine analogs & derivatives
Tetrahydroisoquinolines chemical synthesis
Subjects
Details
- Language :
- English
- ISSN :
- 1477-0539
- Volume :
- 14
- Issue :
- 30
- Database :
- MEDLINE
- Journal :
- Organic & biomolecular chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 27405490
- Full Text :
- https://doi.org/10.1039/c6ob01064d