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Efficient and Versatile Stereoselective Synthesis of Cryptophycins
Author(s) -
Mast Christian Alexander,
Eißler Stefan,
Stončius Arvydas,
Stammler HansGeorg,
Neumann Beate,
Sewald Norbert
Publication year - 2005
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200500282
Subject(s) - stereocenter , dihydroxylation , epimer , stereochemistry , stereoselectivity , epoxide , depsipeptide , enantioselective synthesis , chemistry , catalysis , organic chemistry
The cryptophycins are a family of cyclic depsipeptides with four retrosynthetic units A to D which correspond to the respective amino acids and hydroxy acids. A new synthetic route to unit A allows the selective generation of all four stereogenic centres by introducing two of them in a catalytic asymmetric dihydroxylation, followed by substrate‐controlled diastereoselective reactions. The diol also serves as the epoxide precursor. This approach provides selective access to stereoisomers of unit A (enantiomers, epimers) for structure–activity relationship studies. The unit A derivatives were incorporated into cryptophycin‐1, cryptophycin‐52 and a novel epimer of cryptophycin‐52.