1431570-05-6Relevant articles and documents
A formal approach to the cyanobacterial sunscreen indole, prenostodione
Green, Ilene L.,Jordan, Jason J.,Badenock, Jeanese C.
, p. 183 - 194 (2018)
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.