861695-51-4Relevant academic research and scientific papers
Total Synthesis of Callyspongiolide, Part 2: The Ynoate Metathesis/cis-Reduction Strategy
W?lfl, Bernhard,Mata, Guillaume,Fürstner, Alois
supporting information, p. 255 - 259 (2019/01/04)
The macrocyclic core of the cytotoxic marine natural product callyspongiolide (1) was forged by ring-closing alkyne metathesis (RCAM) of an ynoate precursor using a molybdenum alkylidyne complex endowed with triarylsilanolate ligands as the catalyst. This result is remarkable in view of the failed attempts documented in the literature at converting electron deficient alkynes with the aid of more classical catalysts. The subsequent Z-selective semi-reduction of the resulting cycloalkyne by hydrogenation over nickel boride required careful optimization in order to minimize overreduction and competing dehalogenation of the compound's alkenyl iodide terminus as needed for final attachment of the side chain of 1 by Sonogashira coupling. The required cyclization precursor itself was prepared via Kocienski olefination.
Toward an Asymmetric Synthesis of Bistramide K
Bauder, Claude
, p. 4874 - 4899 (2018/09/10)
The bistramides family has shown antitumoral activity. More specifically bistramide K exhibits lower toxicity than its congeners. In this work, we describe a highly stereoselective and convergent synthesis of two building blocks of the marine metabolite b
Enantioselective total synthesis of octalactin a using asymmetric aldol reactions and a rapid lactonization to form a medium-sized ring
Shiina, Isamu,Hashizume, Minako,Yamai, Yu-Suke,Oshiumi, Hiromi,Shimazaki, Takahisa,Takasuna, Yu-Ji,Ibuka, Ryoutarou
, p. 6601 - 6608 (2007/10/03)
Octalactin A, an antitumor agent containing an eight-memhered lactone moiety, has been stereoselectively prepared by means of enantioselective aldol reactions of selected silyl enolates with achiral aldehydes, promoted by a chiral Sn11 complex.
Asymmetric total synthesis of octalactin B using a new and rapid lactonization
Shiina, Isamu,Oshiumi, Hiromi,Hashizume, Minako,Yamai, Yu-Suke,Ibuka, Ryoutarou
, p. 543 - 547 (2007/10/03)
A method for the synthesis of octalactin B is established via a new and quite effective mixed-anhydride lactonization for the synthesis of an eight-membered ring moiety using 2-methyl-6-nitrobenzoic anhydride with DMAP. Both an optically active linear pre
