17245-25-9Relevant articles and documents
Murray et al.
, p. 1247,1250 (1971)
Total Synthesis of (±)-Exotine B
Cheng, Bichu,Volpin, Giulio,Morstein, Johannes,Trauner, Dirk
, p. 4358 - 4361 (2018)
The heterodimeric indole/coumarin natural product exotine B was synthesized for the first time. The carbon skeleton of the natural product was formed rapidly by a palladium-catalyzed Suzuki cross-coupling reaction and a gallium-catalyzed three-component [
Prenylcoumarins in One or Two Steps by a Microwave-Promoted Tandem Claisen Rearrangement/Wittig Olefination/Cyclization Sequence
Schultze, Christiane,Schmidt, Bernd
, p. 5210 - 5224 (2018/05/17)
The one-pot synthesis of 8-prenylcoumarins from 1,1-dimethylallylated salicylaldehydes and the stabilized ylide [(ethoxycarbonyl)methylene]triphenylphosphorane under microwave conditions was found to have a limited scope. The sequence suffers from a difficult and sometimes low-yielding synthesis of the precursors and from a competing deprenylation upon microwave irradiation. This side reaction occurs in particular with electron rich arenes with two or more alkoxy groups at adjacent positions, a prominent substitution pattern in naturally occurring 8-prenylcoumarins. Both limitations of this one-step sequence were overcome by a two-step synthesis consisting of a microwave-promoted tandem allyl ether Claisen rearrangement/Wittig olefination and a subsequent olefin cross metathesis with 2-methyl-2-butene. The cross metathesis step proceeds with a high selectivity and yields exclusively the desired prenyl, rather than the alternative crotyl substituent. Several naturally occurring 8-prenylcoumarins that were previously inaccessible have been synthesized in good overall yields along this route.
Synthesis of Toddanol and Toddanone
Sharma, Padam N.,Shoeb, Aboo,Kapil, Randhir S.,Popli, Satya P.
, p. 938 - 939 (2007/10/02)
A synthetic approach to confirm the structures of toddanol (1) and toddanone (2) has been provided.In addition, coumurrayin (12), sibiricin (13), isosiribicin (14), toddaculin (8) and aculeatin (9) have also been synthesised.
