Synthesis of tetrahydrobenzo[b]furans via a gold(I)-catalyzed rearrangement/cycloisomerization sequence of cyclic 1-aryl-2-propargyl-cyclohex-2enols
A facile synthesis of tetrahydrobenzo[b]furans via gold(I)-catalyzed cycloisomerization of 1-aryl-2-propargylcyclohex-2-enols is described. The transformation is suggested to proceed through a gold(I)-catalyzed tertiary allylic alcohol rearrangement to gi
Chen, Hsiao-Feng,Yeh, Ming-Chang P.
p. 614 - 629
(2019/02/24)
A bifunctional lewis acid induced cascade cyclization to the tricyclic core of ent-kaurenoids and its application to the formal synthesis of (±)-platensimycin
A mild and efficient bifunctional Lewis acid induced cascade cyclization reaction has been developed for construction of the tricyclic core of ent-kaurenoids. With ZnBr2 as the bifunctional Lewis acid, a series of substituted enones and dienes underwent cascade cyclization smoothly at room temperature and provided the tricyclic products in one pot with good yields (75-91%) and high diastereoselectivity. The cyclized product has been successfully employed for the formal synthesis of (±)-platensimycin.
Zhu, Lizhi,Han, Yejian,Du, Guangyan,Lee, Chi-Sing
supporting information
p. 524 - 527
(2013/04/23)
Formal syntheses of (±)-platensimycin and (±)-platencin via a dual-mode lewis acid induced cascade cyclization approach
A mild and efficient dual-mode Lewis acid induced Diels-Alder (DA)/carbocyclization cascade cyclization reaction has been developed for construction of the tricyclic core of ent-kaurenoids in one pot with the aid of a theoretical study on the π,σ-Lewis acidities of a variety of Lewis acids. With ZnBr2 as the dual-mode Lewis acid, a series of substituted enones and dienes underwent DA/carbocyclization cascade cyclization reaction smoothly at room temperature and provided the tricyclic cyclized products in one pot with good yields and high diastereoselectivity. The tricyclic cyclized product has been successfully utilized as a common intermediate for formal syntheses of (±)-platensimycin and (±)-platencin.
Reductive cyclization of α-cyclopropylketones with alkynyl- and aryl- tethered substituents
Photoinduced electron transfer (PET) reactions of α-cyclopropyl- substituted ketones and triethylamine (TEA) were used to initiate the cyclopropylcarbinyl-homoallyl rearrangement. The intramolecular cyclization reaction onto triple bonds was performed yielding bicyclic and spirocyclic compounds. Furthermore, in some preliminary studies it was shown that even intramolecular aromatic substitutions are feasible.
2,3a,5,6,7,7a-HEXAHYDRO-3H,4H-BENZOTHIOPHENE-3,4-DIONE AND CYCLOPENTA-TETRAHYDROTHIOPHENE-3,4-DIONE ENOLATE ANIONS AS SYNTHETIC EQUIVALENTS TO CYCLOHEX-2-ENONE AND CYCLOPENT-2-ENONE C-2-CARBANIONS.
An efficient procedure for α-alkylation of cyclohex-2-enone and cyclopent-2-enone involving a base-promoted tandem of retrograde Dieckmann-Michael reactions of the C-alkylated derivatives of the title heterocycles is presented.
Baraldi, Pier Giovanni,Barco, Achille,Benetti, Simonetta,Pollini, Gian Piero,Zanirato, Vinicio
p. 4291 - 4294
(2007/10/02)
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