Organic Synthesis: State of the Art 2007 - 2009

By Douglass Taber

Natural synthesis is a colourful and quickly evolving box; we will now cyclize amines at once onto alkenes. just like the first books during this sequence, Organic Synthesis: cutting-edge 2003-2005 and Organic Synthesis: state-of-the-art 2005-2007, this reference leads readers fast to an important contemporary advancements. years of Taber's renowned weekly on-line column, "Organic Chemistry Highlights", as featured at the organic-chemistry.org site, are consolidated the following, with cumulative indices of all 3 volumes during this sequence. vital themes which are coated variety from robust new equipment for C-C bond building to uneven organocatalysis and direct C-H functionalization.

This go-to reference makes a speciality of crucial fresh advancements in natural synthesis, and contains a succinct research of the importance and applicability of every new artificial approach. It info and analyzes greater than twenty complicated overall syntheses, together with the Sammakia synthesis of the Macrolide RK-397, the Ley synthesis of Rapamycin, and the Kobayashi synthesis of (-)-Norzoanthamine.

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NaBH(OAc) O three O 2. LiAlH4 thirteen O Br 14 (racemic) 15 1. OsO4 N O OH 2. Pdcat three. Ac2O 2. DMSO TFAA sixteen AcO AcO CH3O O OCH3 O N N O + H 17 HO AcO O 1. Pdcat O2 H N TsHN O O 18 1. NaBH4 CH3OH O O O H HO + 2. H /H2O H O OCH3 19 N (-)-Drupacine OCH3 This column is devoted to the reminiscence of the overdue John W. Daly, who contributed lots to our wisdom of alkaloid chemistry. 113 57. Stereocontrolled Alkaloid development: Rhazinicine (Gaunt), 9-epi-Pentazocine (Zhai and Li), Fawcettidine (Dake), Strychnine (Padwa), and Yohimbine (Jacobsen) November 24, 2008 the facility of catalytic C-H functionalization is illustrated through the based synthesis of rhazinicine three devised (Angew. Chem. Int. Ed. 2008, forty seven, 3004) by way of Matthew J. Gaunt of the collage of Cambridge. the foremost step within the synthesis used to be the oxidative cyclization of one to two. even if 1 has many C-H websites, the Pd catalyst chosen for the α place of the pyrrole, best, after intramolecular Heck addition and β-hydride removing, to the alkene 2. aid and macrolactamization accomplished the synthesis of three. O CO2Tes H O2N N Me3Si N t-BuOOBz O 1 NH O2N Pd cat Me3Si CO2Tes N O 2 O three (±)-Rhazinicine Hongbin Zhai of the Shanghai Institute of natural Chemistry and Zhong Li of East China collage of technological know-how and know-how ready (Organic Lett. 2008, 10, 2457) the analgesic (-)-9-epi-pentazocine eight from the amino ester four, itself to be had from D-tyrosine. within the conversion of five to six, the (i-PrO)2Ti shaped a hoop, resulting in 6 as a unmarried diastereomer and geometric isomer. HBr then effected either deprotection of the methyl ether and cyclization, to provide 7, which was once carried directly to eight. Bn N NH2. HCl CH3O four CO2CH3 CH3O HBr N SiMe3 five Bn N HO HO 6 i-PrMgCl CH3O Me3Si Bn N Ti(O-i-Pr)4 7 H3C CH3 H3C CH3 eight (-)-9-epi-Pentazocine The Pt-catalyzed cyclization of nine to ten set the level for the synthesis of (+)-fawcettidine 15 via Gregory R. Dake of the college of British Columbia (Angew. Chem. Int. Ed. 2008, forty seven, 4221). This synthesis additionally illustrated the facility of the Ramberg-Bäcklund response for the meeting of medium earrings. The thiolate liberated from 12 without problems extra to the enone, to offer thirteen. 114 STEREOCONTROLLED ALKALOID development Oxidation to the sulfone through the Ramberg-Bäcklund response (halogenation, intramolecular displacement, chelotropic removing of SO2) then brought 14, which used to be selectively decreased, resulting in 15. H N nine S O N O 10 NH S O eleven O NH N 12 S O O O O N O NH O O N S thirteen O O SeO2 PtCl2 cat N 15 (+)-Fawcettidine 14 O Albert Padwa of Emory college has built (J. Org. Chem. 2008, seventy three, 3539) a common path to the Strychnos alkaloids, in keeping with the facile cyclization of the furan sixteen to the tetracyclic ketone 17. This undertaking culminated within the synthesis of the heptacyclic strychnine 20. I N N N OMOM O Ac N N Ac N sixteen O O DMB 17 18 N N Pd(PPh3)4 N DMB PhOK N O O 20 H (±)-Strychnine OMOM 19 H O Eric N.

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