437742-34-2Relevant articles and documents
A Total Synthesis of Salinosporamide A
Marx, Léo B.,Burton, Jonathan W.
, p. 6747 - 6754 (2018)
Salinosporamide A is a β-lactone proteasome inhibitor currently in clinical trials for the treatment of multiple-myeloma. Herein we report a short synthesis of this small, highly functionalized, biologically important natural product that uses an oxidative radical cyclization as a key step and allows for the preparation of gram quantities of advanced synthetic intermediates.
Preparation method and application of Marizomib key intermediate
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, (2020/07/02)
The invention belongs to the field of chemical synthesis, particularly relates to a preparation method and application of a Marizomib key intermediate, and particularly relates to a preparation methodof a Marizomib key intermediate. Natural L-serine is selected as an initial raw material, and an obtained serine fragment protected by a functional group is connected with a 1, 3-dicarbonyl cyclopropyl compound so that the Marizomib key intermediate (a skeleton structure) is prepared, and the preparation method is high in preparation efficiency and yield, safer and more environmentally friendly.Then, the prepared Marizomib key intermediate is used for producing Marizomib, and the Marizomib is obtained through intramolecular cyclization reaction and group modification, protective group removal and structural modification in sequence. Besides, the low-toxicity solvent is used in the whole synthesis process, reagents with high toxicity and difficult preparation are avoided, the solvent consumption is low, the target product recovery rate is high and the stability is good.
Total synthesis of (-)-salinosporamide A
Kaiya, Yuji,Hasegawa, Jun-Ichi,Momose, Takayuki,Sato, Takaaki,Chida, Noritaka
, p. 209 - 219 (2011/10/03)
A detailed description of our second-generation total synthesis of salinosporamideA is presented. Three contiguous stereocenters in the γ-lactam structure seen in the natural product were established by stereoselective functionalization of a D-arabinose scaffold, including an Overman rearrangement to generate a highly congested tetrasubstituted carbon center. One of the definitive reactions in the synthesis was a Lewis acid mediated skeletal rearrangement of a pyranose structure, which enabled the practical conversion of the carbohydrate scaffold to the γ-lactam structure embedded in salinosporamideA. The use of a benzyl ester as a protective group for a sterically hindered carboxylic acid led to a one-pot global deprotection at the end of the synthesis. Rearrange your chemistry! The total synthesis of anticancer natural product salinosporamideA has been achieved through a unique skeletal rearrangement (see scheme). This reaction enabled the construction of the densely functionalized γ-lactam structure found in salinosporamideA through practical methodologies including an Overman rearrangement on a D-arabinose scaffold. Copyright