133744-50-0Relevant articles and documents
Synthesis of Aristotelia-type alkaloids: Syntheses of the natural products (-)-serratenone and (+)-11,12-didehydromakonin-10-one
Galli, Renato,Dobler, Markus,Gueller, Rolf,Stahl, Reto,Borschberg, Hans-Juerg
, p. 3400 - 3413 (2007/10/03)
Two independent total syntheses of the Aristotelia alkaloid (-)-serratenone ((-)-1) are disclosed, one starting with (-)-α-pinene, the other one with (S)-α-terpineol. These correlations led to a revision of the originally proposed absolute configuration of the natural product. In the course of systematic investigations of the behavior of the indole alkaloids (+)-makomakine ((+)-18) and (-)-hobartine ((-)-22) towards oxidizing reagents, it was found that treatment with I2 leads to no less than five different products. Depending on the exact reaction conditions, each of them can be obtained as the major component in yields between 40 and 60%. One of these compounds was shown to be identical with the natural product (+)-11,12-didehydromakonin-10-one ((+)-28).
Synthesis of Aristotelia-type alkaloids. Part XI. Total synthesis of (+)-sorelline and (+)-aristolasene
Dobler,Beerli,Weissmahr,Borschberg
, p. 1411 - 1420 (2007/10/02)
Optically pure samples of the rare Aristotelia alkaloids (+)-sorelline (2) and (+)-aristolasene (3) have been synthesized for the first time. Since natural (S)-perilla alcohol served as one of the starting building blocks, these syntheses delineate the pr
Synthesis of Aristotelia-Type Alkaloids. Part VI. Biomimetic Synthesis of (+)-Aristofruticosine
Beerli, Rene,Borschberg, Hans-Juerg
, p. 110 - 116 (2007/10/02)
(S)-Perilla alcohol (5) was transformed into (S)-7-(phenylthio)-p-menth-1-en-8-amine (11) in five steps.Condensation of this building block with 1-(4-methoxyphenylsulfonyl)-1H-indole-3-acetaldehyde (12) led to the expected imine 15 which cyclized in 54 pe