13861-97-7Relevant articles and documents
2-Siloxy-Substituted Methyl Cyclopropanecarboxylates as Building Blocks in Synthesis: Efficient One-Pot Conversion to γ-Butyrolactones
Grimm, Erich L.,Reissig, Hans-Urlich
, p. 242 - 244 (1985)
A high-yield one-pot transformation to the easily available 2-siloxy-substituted methyl cyclopropanecarboxylates 3 to γ-butyrolactones 5 is described.According to the regioselective preparation of 3, isomeric lactones 5 can be synthesized without problems.Modified procedures delivering α-deuterated or side-chain functionalized lactones are disclosed.
SELECTIVE OXIDATION OF A PRIMARY HYDROXYL IN THE PRESENCE OF SECONDARY ONE
Tomioka, Hiroki,Takai, Kazuhiko,Oshima, Koichiro,Nozaki, Hitosi
, p. 1605 - 1608 (1981)
RuCl2(PPH3)3-benzene system has been found to be highly effective for the title selective oxidation providing 10-hydroxyundecanal in 89percent yield from 1,10-undecanediol.
Structural and stereochemical requirements of the spiroketal group of hippuristanol for antiproliferative activity
Li, Wei,Dang, Yongjun,Liu, Jun O.,Yu, Biao
, p. 3112 - 3115 (2010)
Hippuristanol is a natural product that has recently been shown to inhibit eukaryotic translation initiation and tumor cell proliferation. To investigate the structure and activity relationship of hippuristanol, we synthesized a series of analogs by expan
Synthesis of Lactones via C-H Functionalization of Nonactivated C(sp3)-H Bonds
Richers, Johannes,Heilmann, Michael,Drees, Markus,Tiefenbacher, Konrad
, p. 6472 - 6475 (2016/12/23)
An electron-deficient amide is utilized as a directing group to functionalize nonactivated C(sp3)-H bonds through radical 1,5-hydrogen abstraction. The γ-bromoamides formed are subsequently converted to γ-lactones under mild conditions. The method described is not limited to tertiary and secondary positions but also allows functionalization of primary nonactivated sp3-hybridized positions in a one-pot sequence. In addition, the broad functional group tolerance renders this method suitable for the late-stage introduction of γ-lactones into complex carbon frameworks.
Diverting non-haem iron catalysed aliphatic C-H hydroxylations towards desaturations
Bigi, Marinus A.,Reed, Sean A.,White, M. Christina
scheme or table, p. 216 - 222 (2011/12/16)
Carboxylate-ligated, non-haem iron enzymes demonstrate the capacity for catalysing such remarkable processes as hydroxylations, chlorinations and desaturations of inert, aliphatic C-H bonds. A key to functional diversity is the enzymes' ability to divert fleeting radicals towards different types of functionalization using active site and/or substrate modifications. We report that a non-haem iron hydroxylase catalyst [Fe(PDP)] can also be diverted to catalytic, mixed hydroxylase/desaturase activity with aliphatic C-H bonds. Using a taxane-based radical trap that rearranges under Fe(PDP) oxidation to furnish a nortaxane skeleton, we provide the first direct evidence for a substrate radical using this class of stereoretentive hydroxylation catalysts. Hydroxylation and desaturation proceed by means of a short-lived radical that diverges in a substrate-dependent manner in the presence of carboxylic acids. The novel biomimetic reactivity displayed by this small molecule catalyst is harnessed to diversify natural product derivatives as well as interrogate their biosynthetic pathways.