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Total synthesis of antitumor depsipeptide (-)-doliculide
- Source :
- Organic letters. 3(4)
- Publication Year :
- 2001
-
Abstract
- [reaction: see text] (-)-Doliculide, a potent antitumor agent, is synthesized stereoselectively in a convergent manner. The key strategy involves a stereoselective synthesis of the polyketide unit and synthesis of the D-tyrosine derivative, followed by assembly of the fragments by an esterification and cycloamidation reaction sequence. The synthesis of the polyketide fragment was achieved by an iterative asymmetric synthesis to install stereoselectively both 1,3-dimethyl groups and the 1,3-diol unit by utilizing asymmetric cyclopropanations and Sharpless asymmetric epoxidations as the key steps.
- Subjects :
- Antitumor activity
Depsipeptide
Molecular Structure
Stereochemistry
Organic Chemistry
Enantioselective synthesis
Total synthesis
Antineoplastic Agents
Stereoisomerism
Doliculide
Biochemistry
Combinatorial chemistry
Peptides, Cyclic
chemistry.chemical_compound
Polyketide
chemistry
Cyclization
Depsipeptides
Tyrosine
Stereoselectivity
Physical and Theoretical Chemistry
Derivative (chemistry)
Subjects
Details
- ISSN :
- 15237060
- Volume :
- 3
- Issue :
- 4
- Database :
- OpenAIRE
- Journal :
- Organic letters
- Accession number :
- edsair.doi.dedup.....ec4db6ad9f011a9fe5de7d609a23ea0b