1040731-80-3Relevant academic research and scientific papers
Total synthesis of PDIM A
Nakamura, Tatsuya,Nakagome, Hanae,Sano, Shoichiro,Sadayuki, Tomoko,Hosokawa, Seijiro
, p. 550 - 551 (2016)
Total synthesis of phthiocerol dimycocerosate A (PDIM A), a virulent factor of Mycobacterium tuberculosis, has been achieved. Phthiocerol, a component of PDIM A, has been synthesized by subsequent epoxide-opening alkylation reactions with arabinose-derived diepoxide. This route is concise and efficient in supplying PDIM A for biological studies.
Asymmetric total synthesis of PDIM A: A virulence factor of Mycobacterium tuberculosis
Casas-Arce, Eva,Ter Horst, Bjorn,Feringa, Ben L.,Minnaard, Adriaan J.
supporting information; experimental part, p. 4157 - 4159 (2009/05/07)
The first asymmetric synthesis of phthiocerol was achieved in 15 simple steps and 5.6% overall yield by applying three efficient catalytic transformations. The construction of building block 4 started with the copper/phosphoramidite-catalyzed asymmetric conjugate addition of Me 2Zn to cycloheptenone, followed by in situ ethylation. Baeyer Villiger oxidation using excess m-chloroperoxybenzoic acid (mCPBA) followed by treatment of the resulting lactone 7 with K2C03 in MeOH led to the formation of the linear product. Treatment with TBAF followed by a Fleming-Tamao oxidation using KHCO3 and H2O2, resulted in the formation of the corresponding hydroxy ketones, which could be separated by column chromatography affording 16 as a pure isomers.
