158535-84-3Relevant academic research and scientific papers
Gold(I)-Catalyzed Domino Cyclizations of Diynes for the Synthesis of Functionalized Cyclohexenone Derivatives. Total Synthesis of (-)-Gabosine H and (-)-6-epi-Gabosine H
Vulovic, Bojan,Kolarski, Dusan,Bihelovic, Filip,Matovic, Radomir,Gruden, Maja,Saicic, Radomir N.
supporting information, p. 3886 - 3889 (2016/08/16)
1,6-Diynes with a t-butylcarbonate group in the propargylic position undergo gold(I)-catalyzed domino-cyclization which affords α-hydroxycyclohexenones. The described sequence can be applied on functionalized, highly oxygenated substrates, as examplified
Effective chemoselective deprotection of 3,4-dimethoxybenzyl ( 3,4DMB) ethers in the presence of benzyl and p-methoxybenzyl (PMB) ethers by phenyliodine(III) bis(trifluoroacetate) (PIFA)
Watanabe, Kazuhiro,Katoh, Tadashi
scheme or table, p. 5395 - 5397 (2011/10/18)
In this Letter, a selective deprotection of the alcohol protecting 3,4-dimethoxybenzyl (3,4DMB) group is described. The hypervalent iodine(III) reagent phenyliodine bis(trifluoroacetate) (PIFA) is found to be an efficient reagent for the chemos
An Efficient Method for the Optical Resolution of 3-Hydroxy-2-substituted-4-alkynoates: A Highly Stereoselective Total Synthesis of (+)-Bengamide E
Mukai, Chisato,Kataoka, Osamu,Hanaoka, Miyoji
, p. 5910 - 5918 (2007/10/03)
A novel procedure for the optical resolution of 3-hydroxy-2-substituted-4-alkynoates and its application to the stereoselective total synthesis of (+)-bengamide E are described. 3-Hydroxy-2-substituted-4-alkynoates, derived from the aldol reaction of cobalt-complexed propynals with ketene O-silyl O,S-acetals, were easily resolved by the formation of a chiral carbamate followed by cobalt complexation.Chiral 2-(benzyloxy)-3-hydroxy-4-alkynoate derivatives thus obtained were used as starting materials for a highly stereoselective total synthesis of (+)-bengamide E.
A cobalt-complexed propyanl in organic synthesis: A highly stereoselective total synthesis of bengamide E
Mukai, Chisato,Kataoka, Osamu,Hanaoka, Miyoji
, p. 6899 - 6902 (2007/10/02)
A highly stereoselective aldol reaction of the cobalt-complexed 4-methylpent-2-ynal 2 with O-silyl ketene O,S-acetal 3 provided the syn-aldol product, which was subsequently converted to (+)-bengamide E through optical resolution and the second diastereoselective aldol reaction as crucial steps.
Synthesis of Protected Carbohydrate Derivatives through Homologation of Threose and Erythrose Derivatives with Chiral γ-Alkoxy Allylic Stannanes
Marshall, James A.,Seletsky, Boris M.,Luke, George P.
, p. 3413 - 3420 (2007/10/02)
Additions of the γ-alkoxy allylic stannanes (S)-1 and (R)-1 and the racemate (RS)-1 to the threose and erythrose aldehyde derivatives 6 and 15 in the presence of BF3*OEt2 or MgBr2*OEt2 were examined in order to establish stereochemical preferences.It was found that (S)-1 and aldehyde 6 afforded the syn,anti,syn adduct 7 in the BF3-promoted reaction, while (R)-1 and 6 gave the syn,syn,syn adduct 8 under MgBr2 conditions.Likewise, (S)-1 and aldehyde 15 yielded the syn,anti,anti adduct 16 with BF3, whereas (R)-1 and 15 led to the syn,syn,anti adduct 17 with MgBr2.The MgBr2-promoted reactions showed sufficient rate differences between the matched and mismatched stannanes to allow the use of racemic stannane (RS)-1 in just over 2-fold excess, whereupon the matched adducts 8 and 17 were favored by greater than 9:1 over the mismatched adducts.The major adducts 7, 8, 16, and 17 were converted to the hexose derivatives 21, 30/31, 34, and 39 by ozonolysis, selective deprotection, and refunctionalization.Adducts 16 and 17 were dihydroxylated with OsO4-NMO to the deoxyoctose precursors 40/41 and 42/43.
