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Beilstein J. Org. Chem. 2012, 8, 2060–2066, doi:10.3762/bjoc.8.231
Graphical Abstract
Figure 1: Structures of cryptophycin-1 (1) and -52 (2).
Figure 2: Fluorinated derivatives of cryptophycin-1 and -52 [20-22].
Scheme 1: Access to the trifluoromethyl substituted unit A-building block 16. Reagents and conditions: (a) SO...
Scheme 2: Assembly of units A–D and macrocyclization, followed by diol-epoxide transformation to give the tri...
Scheme 3: Synthesis of the pentafluorophenylalanine building block 26. Reagents and conditions: (a) pyridine,...
Scheme 4: Convergent synthesis of the pentafluorinated cryptophycin 31. Reagents and conditions: (a) Grubbs I...
Beilstein J. Org. Chem. 2011, 7, 243–245, doi:10.3762/bjoc.7.32
Figure 1: The four building blocks (units) A–D of cryptophycin-1 (1) and cryptophycin-52 (2).
Scheme 1: Synthesis of the unit B precursor from D-tyrosine (3). Reagents and conditions [7]: a) SO2Cl2, AcOH, r...
Scheme 2: Unit B synthesis by a chiral PTC approach. Reagents and conditions [9]: a) N-(Diphenylmethylene)glycin...
Scheme 3: Unit B precursor 4 synthesis by asymmetric hydrogenation. Reagents and conditions: a) 3-Chloro-4-me...