11032-05-6Relevant articles and documents
Synthesis of teleocidins A, B and their congeners. Part 3. Synthesis of dihydroteleocidin B-4 (dihydroteleocidin B), teleocidin B-3 and teleocidin B-4
Okabe, Kazuaki,Muratake, Hideaki,Natsume, Mitsutaka
, p. 8559 - 8572 (1991)
Details of the synthesis method of the tumor promoters teleocidin B-3 (3), teleocidin B-4 (4) and dihydroteleocidin B-4 (9) (=dihydroteleocidin B) from (S)- and (R)-methyl N-methyl-N-[7-(3,6,7-trimethyl-1,6-octadien-3-yl)-4-indolyl]-L-valinates (20b and 20a) are presented.
11-Step Total Synthesis of Teleocidins B-1-B-4
Nakamura, Hugh,Yasui, Kosuke,Kanda, Yuzuru,Baran, Phil S.
, p. 1494 - 1497 (2019)
A unified and modular approach to the teleocidin B family of natural products is presented that proceeds in 11 steps and features an array of interesting strategies and methods. Indolactam V, the known biosynthetic precursor to this family, was accessed through electrochemical amination, Cu-mediated aziridine opening, and a remarkable base-induced macrolactamization. Guided by a desire to minimize concession steps, the tactical combination of C-H borylation and a Sigman-Heck transform enabled the convergent, stereocontrolled synthesis of the teleocidins.
A methyltransferase initiates terpene cyclization in teleocidin B biosynthesis
Awakawa, Takayoshi,Zhang, Lihan,Wakimoto, Toshiyuki,Hoshino, Shotaro,Mori, Takahiro,Ito, Takuya,Ishikawa, Jun,Tanner, Martin E.,Abe, Ikuro
supporting information, p. 9910 - 9913 (2014/08/05)
Teleocidin B is an indole terpenoid isolated from Streptomyces. Due to its unique chemical structure and ability to activate protein kinase C, it has attracted interest in the areas of organic chemistry and cell biology. Here, we report the identification of genes encoding enzymes for teleocidin B biosynthesis, including nonribosomal peptide synthetase (tleA), P-450 monooxygenase (tleB), prenyltransferase (tleC), and methyltransferase (tleD). The tleD gene, which is located outside of the tleABC cluster on the chromosome, was identified by transcriptional analysis and heterologous expression. Remarkably, TleD not only installs a methyl group on the geranyl moiety of the precursor but also facilitates the nucleophilic attack from the electron-rich indole to the resultant cation, to form the indole-fused six-membered ring. This is the first demonstration of a cation, generated from methylation, triggering successive terpenoid ring closure.