129649-05-4Relevant academic research and scientific papers
Efficient Syntheses of Traumatic Lactone and Rhizobialide
Zhou, Jing,Song, Shihua,Jiang, Feng,Fu, Chunling,Ma, Shengming
, p. 9948 - 9958 (2019)
Herein, we report the total synthesis of traumatic lactone and rhizobialide by utilizing allenoic acid to construct the lactone ring. The key starting materials, allenoic acids, could be prepared by the ATA (allenation of terminal alkynes) of a terminal alkyne with an aldehyde that contained a protected hydroxyl group followed by hydrolysis. Importantly, the asymmetric synthesis could be realized just by replacing racemic diphenylprinol with (R)- or (S)-diphenylprinol to deliver the optically active allenoate.
Palladium hydroxide catalyzed isomerization of primary allylic alcohols to aldehydes: Application to the formal synthesis of (-)-brevisamide
Sabitha, Gowravaram,Nayak, Sambit,Bhikshapathi,Yadav
supporting information; experimental part, p. 382 - 385 (2011/04/15)
The Pd-catalyzed isomerization of primary allylic alcohols into the corresponding saturated aldehydes has been achieved at room temperature for the first time in good to excellent yields under mild conditions. The functional group compatibility in this reaction is studied, and this new methodology has been successfully applied in the synthesis of a C5-C13 tetrahydropyran ring system of (-)-brevisamide in seven steps.
First stereoselective total synthesis and biological evaluation of amphidinin B and Its analogues
Yadav, Jhillu S.,Reddy, A. Srinivas,Reddy, Ch. Suresh,Reddy, Basi V. Subba,Saddanapu, Venkateshwarlu,Addlagatta, Anthony
experimental part, p. 696 - 706 (2011/04/16)
A highly stereoselective first total synthesis of amphidinin B is described. The key steps involved in this synthesis are the generation of the exo-double bond in the C1-C9 segment, the Barbier allylation, enzymatic kinetic resolutio
The stereoselective total synthesis of (+)-18-(6S,9R,10R)-bovidic acid
Yadav,Ramesh,Subba Reddy,Subba Reddy,Ghamdi, Ahamad Al Khazim Al
scheme or table, p. 2943 - 2945 (2011/06/23)
An expedient stereoselective total synthesis of 18-carbon (+)-(6S,9R,10R)-bovidic acid, isolated from the pelage and skin of a gaur B. frontalis is described using l-proline catalysed sequential α- aminoxylation and Horner-Wadsworth-Emmons olefination of
Combined transition-metal- and organocatalysis: An atom economic C3 homologation of alkenes to carbonyl and carboxylic compounds
Kemme, Susanne T.,Smejkal, Tomas,Breit, Bernhard
supporting information; experimental part, p. 3423 - 3433 (2010/06/21)
A combination of regioselective room-temperature/ambient-pressure hydroformylation (transitionmetal catalysis) and decarboxylative Knoevenagel reactions (organocatalysis) allowed for the development of an efficient, one-pot C3 homologation of terminal alkenes to (E)-α,β-unsaturated acids and esters, (E)-β,γ-unsaturated acids, (E)-α-cyano acrylic acids, and α,β-unsaturated nitriles. All reactions proceed under mild conditions, tolerate a variety of functional groups, and furnish unsaturated carbonyl compounds in good yields and with excellent regioand stereocontrol. Further, an iterative C2 homologation of (E)-α,β-unsaturated carboxylic acids is possible through a combination of decarboxylative hydroformylation employing a supramolecular catalyst followed by decarboxylative Knoevenagel condensation with an organocatalyst.
Stereoselective synthesis of amphidinolide T1
Yadav,Reddy, Ch. Suresh
supporting information; experimental part, p. 1705 - 1708 (2009/08/15)
A highly stereoselective total synthesis of amphidinolide T1 is achieved using Sharpless asymmetric epoxidation, base-induced epoxide opening, radical cyclization, diastereoselective reduction followed by allylation, Evans methylation, base-induced reduct
Practical synthesis of (E)-α,β-unsaturated carboxylic acids using a one-pot hydroformylation/decarboxylative Knoevenagel reaction sequence
Kemme, Susanne T.,?mejkal, Tomá?,Breita, Bernhard
supporting information; experimental part, p. 989 - 994 (2009/05/27)
Combining the regioselective room temperature/ambient pressure hydroformylation and a modification of the Doebner-Knoevenagel reaction allowed for the development of an efficient, one-pot procedure for the synthesis of (E)-α,β-unsaturated carboxylic acids. The reaction proceeds under mild conditions, tolerates a variety of functional groups and gives (E)-α,β-unsaturated carboxylic acids in good yields and with excellent regio-and stereocontrol. The practicability of this process has been demonstrated by a short protecting group-free synthesis of the queen honeybee pheromones 9-ODA[( E)-9-oxodec-2-enoic acid] and 9-HDA[( E)-9-hydroxydec-2-enoic acid].
First asymmetric total synthesis of penarolide sulfate A1
Mohapatra, Debendra K.,Bhattasali, Debabrata,Gurjar, Mukund K.,Khan, M. Islam,Shashidhara
experimental part, p. 6213 - 6224 (2009/05/31)
Penarolide sulfate A1, with three contiguous stereogenic centers on a macrocyclic skeleton, affords promise as an α-glucosidase inhibitor. Herein, we describe the first asymmetric total synthesis of this natural product. A stereoselective strat
Asymmetric synthesis of 2,4,5-trisubstituted piperidines from sulfinimine-derived δ-amino β-ketoesters. Formal synthesis of pseudodistomin B triacetate
Davis, Franklin A.,Zhang, Junyi,Li, Yingxin,Xu, He,DeBrosse, Charles
, p. 5413 - 5419 (2007/10/03)
N-Sulfinyl δ-amino β-ketoester enaminones, a new sulfinimine-derived chiral building block, undergoes, on hydrolysis in one pot, an intramolecular Michael addition followed by a retro-Michael-type elimination to give enantiopure 2,4,5-trisubstituted piper
Bidentate ligands by self-assembly through hydrogen bonding: A general room temperature/ambient pressure regioselective hydroformylation of terminal alkenes
Seiche, Wolfgang,Schuschkowski, Alexander,Breit, Bernhard
, p. 1488 - 1494 (2007/10/03)
The 6-DPPon (1)/rhodium catalyst allows for the first time a room temperature/ambient pressure regioselective hydroformylation of terminal alkenes with low catalyst loadings in good activity. The generality of this catalyst under these conditions was demonstrated for a wide range of structurally diverse alkenes equipped with many important functional groups. Thus, this practical and highly selective hydroformylation protocol, which omits the need for special pressure equipment, should find wide application in organic synthesis.
