35891-70-4Relevant articles and documents
Construction of Quaternary Carbon Stereocenter of α-Tertiary Amine through Remote C-H Functionalization of Tris Derivatives: Enantioselective Total Synthesis of Myriocin
Miyagawa, Takashi,Inuki, Shinsuke,Oishi, Shinya,Ohno, Hiroaki
, p. 5485 - 5490 (2019)
We describe the development of a strategy for the construction of the quaternary carbon stereocenter of α-tertiary amines. This strategy highlights a site-selective C-H functionalization involving an alkoxy-radical-triggered 1,5-hydrogen transfer (1,5-HAT
Total synthesis of myriocin and mycestericin D employing Rh(II)-catalyzed C[sbnd]H amination followed by stereoselective alkylation
Noda, Narumi,Nambu, Hisanori,Ubukata, Kana,Fujiwara, Tomoya,Tsuge, Kiyoshi,Yakura, Takayuki
, p. 868 - 878 (2017/01/28)
Total synthesis of myriocin and mycestericin D was achieved using the Du Bois Rh(II)-catalyzed C[sbnd]H amination of a sulfamate and subsequent alkylation as a key step. The reaction of a sulfamate with PhI(OAc)2and MgO in the presence of Rh2(OAc)4gave oxathiazinane N,O-acetal as the sole product in high yield. Alkylation of N,O-acetal using vinylmagnesium bromide in the presence of ZnCl2proceeded stereoselectively to provide an oxathiazinane bearing a quaternary chiral center in high yield. Myriocin and mycestericin D were synthesized from a common synthetic intermediate. This route includes the first application of the Du Bois procedure for constructing a quaternary chiral center.
Total synthesis of the immunosuppressants myriocin and 2-epi-myriocin
Jones, Matthew C.,Marsden, Stephen P.
supporting information; experimental part, p. 4125 - 4128 (2009/05/27)
(Chemical Equation Presented) Total syntheses of the natural immunosuppressant myriocin (1) and the equipotent unnatural analogue 2-epi-myriocin (in protected form) have been achieved through a common strategy. The key transformations are the efficient synthesis of a quaternary (E)-vinylglycine by asymmetric deconjugative alkylation of a dehydroamino acid and an unusually highly diastereoselective dihydroxylation of the vinylglycine alkene.
Total synthesis of myriocin
Lee, Kee-Young,Oh, Chang-Young,Kim, Yong-Hyun,Joo, Jae-Eun,Ham, Won-Hun
, p. 9361 - 9363 (2007/10/03)
A concise, stereocontrolled synthesis of myriocin was achieved. Key features involve diastereoselective oxazoline formation catalyzed by palladium(0), MgBr2-promoted allylic stannane addition, and palladium(0)-catalyzed coupling of a vinyl iodide with an organozinc reagent.
Total synthesis of (+)-myriocin and (-)-sphingofungin E from aldohexoses using overman rearrangement as the key reaction
Oishi, Takeshi,Ando, Koji,Inomiya, Kenjin,Sato, Hideyuki,Iida, Masatoshi,Chida, Noritaka
, p. 1927 - 1947 (2007/10/03)
Total synthesis starting from aldohexoses of naturally occurring α-substituted α-amino acids, (+)-myriocin (1) and (-)-sphingofungin E (2), is described. Overman rearrangement of allylic trichloroacetimidate 6E derived from D-mannose effectively generated the tetrasubstituted carbon with nitrogen, and subsequent Wittig olefination afforded the highly functionalized moiety 3 of myriocin stereoselectively. Sulfone-mediated coupling reaction of the allyl bromide 3 with C12 hydrophobic part 4 successfully constructed the carbon framework possessing E-olefin 28. Removal of the sulfone and protecting groups completed the chiral and stereoselective total synthesis of (+)-myriocin (1). A similar transformation starting from D-glucose also accomplished the total synthesis of (-)-sphingofungin E (2).
Stereoselective total synthesis of (+)-myriocin from D-mannose
Oishi,Ando,Chida
, p. 1932 - 1933 (2007/10/03)
The stereoselective total synthesis of myriocin 1 from D-mannose is described; the carbon framework with three contiguous chiral centers including a tetra-substituted carbon with nitrogen was effectively constructed using Overman rearrangement as the key
A novel enantioselective synthesis of (+)-myriocin based on the chemistry of 1-trimethylsilylbuta-2,3-dienes
Hatakeyama, Susumi,Yoshida, Masashi,Esumi, Tomoyuki,Iwabuchi, Yoshiharu,Irie, Hiroshi,Kawamoto, Toshiki,Yamada, Hidetoshi,Nishizawa, Mugio
, p. 7887 - 7890 (2007/10/03)
A synthesis of (+)-myriocin has been achieved in a highly stereoselective manner employing TiCl4 catalyzed addition of 1- trimethylsilylbuta-2,3-diene to an aldehyde and Et2AICI catalysed cyclization of an epoxytrichloroacetimidate f
Asymmetric Total Synthesis of ISP-I (Myriocin, Thermozymocidin), a Potent Immunosuppressive Principle in the Isaria sinclairii Metabolite
Shigeki, Sano,Kobayashi, Yoshimaro,Kondo, Tatsuya,Takebayashi, Maki,Maruyama, Shigeki,et al.
, p. 2097 - 2100 (2007/10/02)
Asymmetric total synthesis of ISP-I has been achived by utilizing highly selectrive E-olefin formation based on the Schlosser-modified Wittig reaction and highly diastereoselective aldol reactions employing both chiral heterocyclic derivatives, 3-acetyl-(4S)-isopropyl-1,3-thiazolidine-2-thione and ethyl -2-yl carboxylate.
Total Syntheses of Myriocin and Z-Myriocin, Two Potent Immunosuppressants, from 2-Deoxy-D-Glucose
Yoshikawa, Masayuki,Yokokawa, Yoshihiro,Okuno, Yasuhiro,Murakami, Nobutoshi
, p. 6209 - 6228 (2007/10/02)
Total syntheses of myriocin (thermozymocidin, ISP-1, 21) and its analog, Z-myriocin (22), which showed potent immunosuppressive activity, were accomplished starting from 2-deoxy-D-glucose by employing a modified Darzen reaction as a key reaction.The stereoselectivity of the modified Darzen reaction for six-membered cyclic ketones was discussed on the basis of physicochemical evidence including the conformational analyses of the cyclic ketones based on molecular mechanics calculation.
Total synthesis of a novel immunosuppressant, myriomicin (thermozymocidin, ISP-I), and Z-myriocin
Yoshikawa,Yokokawa,Okuno,Murakami
, p. 994 - 996 (2007/10/02)
Myriocin (thermozymocidin, ISP-I), which was known to exhibit several interesting biological properties such as potent immunosuppressive and antifungal activities, and a new analog Z-myriocin were synthesized from 2-deoxy-D-glucose. This synthetic pathway comprises a stereoselective formation of the chiral α,α-disubstituted amino acid structure in myriocin and Z-myriocin from the isopropylidene six-membered ketone by using a modified Darzen reaction as its key step.
