87604-58-8Relevant articles and documents
A Br?nsted Acid Catalyzed Cascade Reaction for the Conversion of Indoles to α-(3-Indolyl) Ketones by Using 2-Benzyloxy Aldehydes
Banerjee, Ankush,Maji, Modhu Sudan
supporting information, p. 11521 - 11527 (2019/08/16)
A Br?nsted acid catalyzed, operationally simple, scalable route to several functionalized α-(3-indolyl) ketones has been developed and the long-standing regioisomeric issue has been eliminated by choosing appropriate carbonyls. A readily available and cheap bottle reagent was used as the catalyst. This protocol was also applicable to the synthesis of densely functionalized α-(3-pyrrolyl) ketones. A detailed mechanistic study confirmed the involvement of enolether as a reaction intermediate. Several postsynthetic modifications along with easy access to β-carboline, tryptamines, tryptophols, and spiro-indolenine proclaim the synthetic utility of this powerful building block. On the basis of this concept, functionalized carbazoles were constructed by a cascade annulation strategy.
Stereoselective total synthesis of verbalactone
Alluraiah, Gurrala,Sreenivasulu, Reddymasu,Sreenivasa Murthy, Indraganti,Ramesh Raju, Rudraraju
, p. 2019 - 2024 (2015/02/19)
A simple and efficient route for the stereoselective total synthesis of verbalactone from commercially available inexpensive starting material d-mannitol using Barbier allylation, α-aminoxylation, and Yamaguchi macrolactonization as key steps is reported.
Stereoselective synthesis of (S)-oxiracetam and (S)-GABOB from (R)-glyceraldehyde acetonide
Sanyal, Ishita,Shukla, Brajesh,Barman, Piyali Deb,Banerjee, Asish Kumar
, p. 2637 - 2640 (2013/06/26)
Synthetic routes to (S)-oxiracetam and (S)-GABOB have been developed starting from (R)-glyceraldehyde acetonide through its conversion to an appropriate aldehyde intermediate followed by reductive amination using glycinamide hydrochloride/benzyl amine and subsequent chemical transformations.
Enantioselective total synthesis of brevetoxin A: Unified strategy for the B, E, G, and J subunits
Crimmins, Michael T.,Ellis, J. Michael,Emmitte, Kyle A.,Haile, Pamela A.,McDougall, Patrick J.,Parrish, Jonathan D.,Zuccarello, J. Lucas
supporting information; experimental part, p. 9223 - 9234 (2010/04/25)
Brevetoxin A is a decacyclic ladder toxin that possesses 5-, 6-, 7-, 8-, and 9-membered oxacycles, as well as 22 tetrahedral stereocenters. Herein, we describe a unified approach to the B, E, G, and J rings based upon a ring-closing metathesis strategy from the corresponding dienes. The enolate technologies developed in our laboratory allowed access to the precursor acyclic dienes for the B, E, and G medium-ring ethers. The strategies developed for the syntheses of these four monocycles ultimately provided multigram quantities of each of the rings, supporting our efforts toward the completion of a convergent synthesis of brevetoxin A.
Enantioselective total synthesis of bistramide A
Crimmins, Michael T.,DeBaillie, Amy C.
, p. 4936 - 4937 (2007/10/03)
The enantioselective synthesis of bistramide A has been achieved with a longest linear sequence of 18 steps. The synthetic strategy involves the use of a distereoselective glycolate alkylation, an aldol addition of a chlorotitanium enolate of N-acylthiazolidinthione, and a Sharpless asymmetric epoxidation to synthesize the three key fragments. Copyright
A convergent coupling strategy for the formation of polycyclic ethers: Stereoselective synthesis of the BCDE fragment of brevetoxin A
Crimmins, Michael T.,McDougall, Patrick J.,Emmitte, Kyle A.
, p. 4033 - 4036 (2007/10/03)
(Chemical Equation Presented) A stereoselective synthesis of the BCDE fragment of brevetoxin A has been completed. anti-Glycolate aldol, glycolate alkylation, and ring-closing metathesis reactions were employed as key bond-forming events. A convergent ass
Diastereo- and enantioselective synthesis of 1,2-amino alcohols and protected α-hydroxy aldehydes from glycol aldehyde hydrazones
Enders, Dieter,Reinhold, Ulrich
, p. 11 - 26 (2007/10/03)
Starting from chiral glycol aldehyde hydrazones (S)-2, we prepared differently protected α-hydroxy aldehydes (R)- or (S)-4 as well as N-acetyl-protected 1,2-amino alcohols (R)-11 in high enantiomeric excesses via azaenolate α-alkylation or nucleophilic 1,2-addition to the CN double bond. The successive introduction of two vicinal stereogenic centres opens a new, flexible syn-diastereo- and enantioselective route to functionalised, N-acetyl-protected, vicinal amino alcohols (R,R)-13, which was demonstrated in the case of the γ-amino-β-hydroxycarboxylic acid statin (R,R)-15 and its analogues B. VCH Verlagsgesellschaft mbH, 1996.
Asymmetric synthesis of α-substituted nitriles and cyanohydrins by oxidative cleavage of chiral aldehyde hydrazones with magnesium monoperoxyphthalate
Enders, Dieter,Plant, Andrew,Backhaus, Dirk,Reinhold, Ulrich
, p. 10699 - 10714 (2007/10/02)
Optically active α- and α,β-substituted aldehyde hydrazones 2, 4, and 7, which are readily available by assymmetric alkylation, Michael addition or [2,3]-Wittig rearrangement of chiral hydrazones can be transformed into nitriles 3 and 5 or cyanohydrins 8 by MMPP mediated oxidation, respectively. This synthetic sequence offers a C-C connective entry into optically active functionalised nitriles with good overall yields (30-75%) together with high diastereo- and enantioselectivities (de = 76 - ≥ 96%, ee ≥ 72 - ≥ 97%).
Enantioselective Synthesis of the Bottom Half of Chlorothricolide. 3. Studies of the Steric Directing Group Strategy for Stereocontrol in Intramolecular Diels-Alder Reactions
Roush, William R.,Kageyama, Masanori,Riva, Renata,Brown, Bradley B.,Warmus, Joseph S.,Moriarty, Kevin J.
, p. 1192 - 1210 (2007/10/02)
The intramolecular Diels-Alder reactions of a series of C(7)-alkoxy-substituted 2(E),8(Z),10(E)-undecatrienoates and trienals containing removable C(9)-Br or C(9)-SiMe3 substituents (11, 12, 13, 33, 42, 43, 44, 45) were studied as part of a programm direc
ON THE STERIC COURSE OF THE ADDITION OF SOME ORGANOMETALLIC REAGENTS TO (R)-2,3-ISOPROPYLIDENE GLYCERALDEHYDE. SYNTHESIS OF OPTICALLY ACTIVE α-BENZYLOXY ALDEHYDES, ALCOHOLS, CARBOXYLIC ACIDS AND 1,2-DIOLS.
Mulzer, Johann,Angermann, Alfred
, p. 2843 - 2846 (2007/10/02)
Organo-titanium and organo-zinc reagents were added stereoselectively to (R)-2,3-isopropylidene glyceraldehyde (1) to give the alcohols 2/3, which were converted into the optically active derivatives 4-11.
