- Regiodivergent Remote Arylation of Cycloalkanols to Dysideanone′s Fused Carbotetracycles and Its Bridged Isomers
-
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.
- Haque, Md Ashraful,Jana, Chandan K.
-
-
Read Online
- Synthesis of phosphatidylinositol 3-kinase (PI3K) inhibitory analogues of the sponge meroterpenoid liphagal
-
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
- 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)
-
- Total synthesis of (-)-hispanolone and an improved approach towards prehispanolone
-
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)-
- Cheung, Wing Shun,Wong, Henry N. C.
-
p. 11001 - 11016
(2007/10/03)
-
- Total syntheses of naturally occurring molecules possessing 1,7- dioxaspiro[4.4]nonane skeletons
-
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.
- Wong, Henry N. C.
-
p. 1757 - 1765
(2007/10/03)
-
- Total synthesis of a monocyclofarnesane norsesquiterpenoid isolated from mushroom ingested by beetle: Utility of solid state Baeyer-Villiger oxidation
-
Norsesquiterpenoid 1 has been synthesised starting from (S)-(+)-Wieland-Miescher ketone analogue 3 via solid state Baeyer-Villiger oxidation as a key step.
- Hagiwara, Hisahiro,Nagatomo, Hidenori,Kazayama, Shin-Ichi,Sakai, Hitoshi,Hoshi, Takashi,Suzuki, Toshio,Ando, Masayoshi
-
p. 457 - 459
(2007/10/03)
-