60066-61-7Relevant articles and documents
Total Synthesis of (-)-Isoschizogamine
Takada, Akihiro,Fujiwara, Hiroaki,Sugimoto, Kenji,Ueda, Hirofumi,Tokuyama, Hidetoshi
, p. 16400 - 16403 (2015)
The total synthesis of (-)-isoschizogamine was accomplished, featuring the construction of the quaternary carbon center by the modified Johnson-Claisen rearrangement in basic media and the facile assembly of the key tetracyclic quinolone intermediate through a cascade cyclization. The characteristic cyclic aminal was constructed by late-stage C-H functionalization at the position adjacent to the lactam nitrogen using a combination of CrO3 and nBu4NIO4 and subsequent Bi(OTf)3-mediated cyclization.
Atmospheric Oxygen Mediated Radical Hydrothiolation of Alkenes
McCourt, Ruairí O.,Scanlan, Eoin M.
supporting information, p. 15804 - 15810 (2020/10/26)
A mild, metal-free, atmospheric oxygen-mediated radical hydrothiolation of alkenes (and alkyne) is reported. A variety of sulfur containing motifs including alkanethiols, thiophenols and thioacids undergo an atmospheric oxygen-mediated radical hydrothiolation reaction with a plethora of alkenes in good yield with excellent functional group compatibility, typically with short reaction times to furnish a range of functionalized products. Biomolecules proved tolerant to the conditions and the procedure is robust and easily executable requiring no specialized equipment. Concise mechanistic studies confirm the process proceeds through radical intermediates in a thiol-ene reaction manifold. The methodology offers an efficient “green” approach for thiol-ene mediated “click” ligation and a milder alternative to thermally initiated hydrothiolation processes.
Synthesis of 5-[(Pentafluorosulfanyl)methyl]-γ-butyrolactones via a Silver-Promoted Intramolecular Cyclization Reaction
Roudias, Majdouline,Gilbert, Audrey,Paquin, Jean-Fran?ois
, p. 6655 - 6665 (2019/11/03)
The synthesis of 5-[(pentafluorosulfanyl)methyl]-γ-butyrolactones bearing different substituents at position 3 or 4 is reported. A silver-promoted intramolecular cyclization of substituted 4-chloro-5-(pentafluorosulfanyl)pentanoic acids allows the preparation of the substituted SF5-containing γ-butyrolactones in up to 96 % yield.