128461-65-4Relevant articles and documents
Synthesis of tetrahydrofurans from protected β-hydroxyaldehydes: Optimization of the alcohol protecting group
Angle, Steven R.,Bernier, Daniel S.,El-Said, Nahla A.,Jones, Darin E.,Shaw, Stephanie Z.
, p. 3919 - 3922 (1998)
As part of an effort to generalize the synthesis of substituted tetrahydrofurans from protected β-hydroxy aldehydes, a series of common alcohol protecting groups was screened for compatibility with the methodology. Employing a β-(triisopropylsilyloxy)alde
Stereoselective synthesis of (-)-pinidinone
Shankaraiah, Gundeti,Vijaya Kumar, Tiruvayamudi,Venkateswara Reddy, Guvvala,Madhusudana Rao, Janaswamy,Suresh Babu, Katragadda
, p. 990 - 996 (2013)
A simple and efficient stereoselective linear approach to the total synthesis of (-)-pinidinone has been accomplished starting from propane-1,3-diol, and employing Maruoka asymmetric allylation and Grubbs' olefin cross-metathesis as the key steps. Copyright
Modular Total Synthesis of iso-Archazolids and Archazologs
Scheeff, Stephan,Rivière, Solenne,Ruiz, Johal,Dedenbach, Simon,Menche, Dirk
, p. 10190 - 10223 (2021/08/16)
Full details on the design, development, and successful implementation of suitable synthetic strategies directed toward the total synthesis of iso-archazolids and archazologs are reported. Both a biomimetic and a multistep total synthesis of iso-archazolid B, the most potent and least abundant archazolid, are described. The bioinspired conversion from archazolid B was realized by a high-yielding 1,8-Diazabicyclo[5.4.0]undec-7-ene catalyzed one-step double-bond shift. A highly stereoselective total synthesis was accomplished in 25 steps, involving a sequence of highly stereoselective aldol reactions, an efficient aldol condensation to forge two elaborate fragments, and a challenging ring-closing metathesis macrocyclization with an unusual Stewart-Grubbs catalyst. These strategies proved to be generally useful and could be successfully implemented for the preparation of three novel iso-archazolids as well as five novel archazologs, lacking the thiazole side chain. A wide variety of further archazolids and archazologs may now be targeted for exploration of the promising anticancer potential of these polyketide macrolides.
BIOCATALYTIC SYNTHESIS OF CRYPTOPHYCIN ANTICANCER AGENTS
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, (2021/04/02)
The disclosure provides cryptophycin intermediates, cryptophycin analogs, and cryptophycin chimeric molecules useful in treating cancer, as well as methods of producing these compounds and methods of treating cancer.