1431570-01-2Relevant articles and documents
Pd-Catalyzed Dearomative Carboxylation of Indolylmethanol Derivatives
Mita, Tsuyoshi,Ishii, Sho,Higuchi, Yuki,Sato, Yoshihiro
supporting information, p. 7603 - 7606 (2018/12/11)
By using a new catalytic system (PdCl2[P(n-Bu)3]2 in combination with ZnEt2), various 3-indolylmethanol derivatives were successfully carboxylated with CO2 (1 atm) via dearomatization of the indole nucleus, affording 3-methyleneindoline-2-carboxylates. In contrast, carboxylation of 2-indolylmethanol derivatives afforded unexpected doubly carboxylated products, which are useful synthetic precursors for biologically active compounds.
A formal approach to the cyanobacterial sunscreen indole, prenostodione
Green, Ilene L.,Jordan, Jason J.,Badenock, Jeanese C.
, p. 183 - 194 (2018/06/27)
The synthesis of the indole sunscreen pigment prenostodione was attempted via an LDA-initiated condensation of N-carbamate indole-2-methyl ester 22 with 4-[(t-butyldimethylsilyl)oxy]benzaldehyde (14) and a late-stage Vilsmeier-Haack formylation. Difficulties with the ensuing oxidation required installation of a C-3 carboxylic acid necessitating the use of a recently reported protocol and thus a formal synthesis of the natural product was realized from 2-aminobenzyl alcohol (17) in nine steps.
Synthetic approaches toward the marine alkaloid prenostodione
Badenock, Jeanese C.,Jordan, Jason A.,Gribble, Gordon W.
, p. 2759 - 2762 (2013/06/05)
An efficient synthesis of the core of prenostodione (3) is described herein featuring the base condensation of BOC-protected indole diesters 21 and 24 with p-methoxybenzaldehyde (22) and 4-[(t-butyldimethylsilyl)oxy]benzaldehyde (26). Attempts at selective saponification of the resultant diesters yielded isoprenostodione (3a) bearing the ester functionality at the C-3 position of the indole ring.