18455-03-3Relevant academic research and scientific papers
Synthesis and biological evaluation of (±)-hippolachnin and analogs
Winter, Nils,Rupcic, Zeljka,Stadler, Marc,Trauner, Dirk
, p. 375 - 383 (2019/04/26)
Due its unique structure and its reported potent antifungal activity, the marine polyketide hippolachnin A (1) has attracted much attention in the synthetic community. Herein, we describe the development of a concise, diversifiable and scalable synthesis of the racemic natural product, which serves as a platform for the generation of bioactive analogues. Biological testing of our synthetic material did not confirm the reported antifungal activity of hippolachnin A but unraveled moderate activity against nematodes and microbes.
HYDRATION OF 1-METHOXY-cis-BICYCLOHEPT-3,6-DIEN-2-ONE CATALYSED BY BOVINE SERUM ALBUMINE. THE SYNTHESIS OF OPTICALLY ACTIVE 1-METHOXY-4-exo-HYDROXY-cis-BICYCLOHEPT-6-EN-2-ONE
Cavazza, Marino,Zandomeneghi, Maurizio,Viti, Andrea Ermete
, p. 799 - 802 (2007/10/02)
Bovine serum albumine rapidly binds (-)(1S,5R)-1-methoxy-cis-bicyclohept-3,6-dien-2-one and catalyses the hydration of the enone to 1-methoxy-4-exo-hydroxy-cis-bicyclohept-6-en-2-one optically enriched in the (+)(1R,4R,5S)-stereoisomer.Chiroptical data for the hydrated compound are deduced.
Light-induced Synthesis of 3-Alkyltropones
Cavazza, Marino,Pietra, Francesco
, p. 2283 - 2288 (2007/10/02)
Irridation of 4-acetoxycyclopent-2-en-1-one (1) and hex-1-yne (8) with Pyrex-filtered light of a Hg lamp, followed by AcOH elimination with alumina, gave 3-n-butyltropone (15), via intermediate 4-acetoxy-7-n-butyl-cis-bicyclohept-6-en-1-one (10) and 1-n-butyltricyclo2,7>hept-4-en-3-one (13) in 21percent overall, unoptimized yield whereas when 350 and 363 nm laser light was used, only compound (10) was formed and was isolated as 7-n-butyl-cis-bicyclohepta-3,6-dien-1-one (11). 3-(2'-Hydroxyprop-2'-yl)tropone (16), similarly prepared from compound (1) and 2-methylbut-3-yn-2-ol (9), was dehydrated to give 3-isopropenyltropone (17), a synthetic precursor of β-dolabrin (18). 3-Methoxytropone (23) was similarly synthesized.
Synthetic Photochemistry. XIII. Chiroptical Retention for the Reported "antara-antara"-3,3-Sigmatropy of Bicyclohepta-3,6-dien-2-ones
Takeshita, Hitoshi,Kumamoto, Masatoshi,Kuono, Isao
, p. 1006 - 1009 (2007/10/02)
Troponoids were shown to form 2:1-complexes with β-cyclodextrin and 1:1 complexes with α-cyclodextrin.The photoisomerization of complexed tropolone and 2-methoxytropone gave optically active 1-hydroxy- and 1-methoxybicyclohepta-3.6-dien-2-ones in improved yields.The pyrolysis of the (+)-1-methoxybicyclohepta-3,6-dien-2-one gave the (+)-3-methoxybicyclohepta-3,6-dien-2-one, ruling out the two-fold supra-antara-1,3-sigmatropy.
