224048-24-2Relevant academic research and scientific papers
Regiodivergent Remote Arylation of Cycloalkanols to Dysideanone′s Fused Carbotetracycles and Its Bridged Isomers
Haque, Md Ashraful,Jana, Chandan K.
, p. 13300 - 1330 (2017)
Regiodivergent γ and γ′ arylations across an all-carbon quaternary center of cycloalkanols to access enantioenriched fused and bridged carbotetracycles are reported. The conformation of the carbocation guided either sequential stereospecific β-C-Me/γ-C?H-shifts or β-C-Me/γ′-C?H-shifts, providing fused carbotetracyclic analogs of dysideanone or bridged tetracycles, respectively. The reaction is highly stereoselective in building three contiguous stereocenters, where one, two, or three could be all-carbon quaternary centers. Interestingly, mechanistic studies revealed a crucial role of a methyl substituent in controlling regioselectivity.
Synthesis of phosphatidylinositol 3-kinase (PI3K) inhibitory analogues of the sponge meroterpenoid liphagal
Pereira, Alban R.,Strangman, Wendy K.,Marion, Frederic,Feldberg, Larry,Roll, Deborah,Mallon, Robert,Hollander, Irwin,Andersen, Raymond J.
, p. 8523 - 8533 (2011/02/26)
Analogues of the sponge meroterpenoid liphagal (1) have been synthesized and evaluated for inhibition of PI3Kα and PI3Kα as part of a program aimed at developing new isoform-selective PI3K inhibitors. One of the analogues, compound 24, with IC50/sub
Total synthesis of a monocyclofarnesane norsesquiterpenoid isolated from mushroom ingested by beetle: Utility of solid state Baeyer-Villiger oxidation
Hagiwara, Hisahiro,Nagatomo, Hidenori,Kazayama, Shin-Ichi,Sakai, Hitoshi,Hoshi, Takashi,Suzuki, Toshio,Ando, Masayoshi
, p. 457 - 459 (2007/10/03)
Norsesquiterpenoid 1 has been synthesised starting from (S)-(+)-Wieland-Miescher ketone analogue 3 via solid state Baeyer-Villiger oxidation as a key step.
Total synthesis of (-)-hispanolone and an improved approach towards prehispanolone
Cheung, Wing Shun,Wong, Henry N. C.
, p. 11001 - 11016 (2007/10/03)
On the basis of the recently reported construction of (±)-hispanolone (2), the enantiomerically pure form of (-),2, employed in our partial synthesis of the specific platelet activating factor receptor antagonist prehispanolone (3), was prepared from (S)-
Total syntheses of naturally occurring molecules possessing 1,7- dioxaspiro[4.4]nonane skeletons
Wong, Henry N. C.
, p. 1757 - 1765 (2007/10/03)
The syntheses of several naturally occurring molecules, namely prehispanolone, sphydrofuran, secosyrins, and syringolides are reviewed. Interestingly, these compounds are all structurally related, possessing a 1,7-dioxaspiro[4.4]nonane framework. The pivotal step in these synthetic endeavors involves the peracid oxidation of substituted 2- trimethylsilylfurans to but-2-en-4-olides. A subsequent intramolecular Michael addition procedure was also essential in the construction of the spiro skeleton. Two significant issues concerning regioselectivity and stereoselectivity are also addressed.
