164577-87-1Relevant academic research and scientific papers
Total synthesis of the marine alkaloids (-)-lepadins A, B, and C based on stereocontrolled intramolecular acylnitroso-diels-alder reaction
Ozawa,Aoyagi,Kibayashi
, p. 3338 - 3347 (2001)
The first syntheses of (-)-lepadins A and C, as well as a new synthesis of (-)-lepadin B, have been achieved from commercially available (S)-malic acid. The methodology is based on an intramolecular hetero-Diels-Alder reaction of the acylnitroso compound, affording the bicyclic oxazino lactam with trans selectivity, which was converted to the cis-decahydroquinoline via asymmetric enolate hydroxylation followed by intramolecular aldol cyclization. The total syntheses proceed by employing cis-decahydroquinoline bearing the (E)-iodoalkenyl group as the common key intermediate, which underwent a convergent coupling with the (E)-hexenyl unit via a palladium-catalyzed Suzuki cross-coupling reaction for the elaboration of the octadienyl side chain at the C5 position.
A new synthetic strategy for 2-deoxy-D-ribose via palladium(II)-catalyzed cyclization of aldehyde
Miyazawa, Masahiro,Awasaguchi, Ken-Ichiro,Uoya, Ikuyo,Yokoyama, Hajime,Hirai, Yoshiro
, p. 1891 - 1902 (2011/04/12)
We achieved a total synthesis of 2-deoxy-D-ribose through intramolecular Pd(II)-catalyzed cyclization of aldehyde via an unstable hemiacetal intermediate as a key step. The Japan Institute of Heterocyclic Chemistry.
Total synthesis of the marine alkaloid (-)-lepadin B.
Ozawa,Aoyagi,Kibayashi
, p. 2955 - 2958 (2007/10/03)
An enantioselective total synthesis of (-)-lepadin B has been developed starting from (2S,4S)-2,4-O-benzylidene-2, 4-dihydroxybutanal. The key steps in the synthesis include the use of an aqueous intramolecular acylnitroso Diels-Alder reaction to afford t
Stereoselective Synthesis of Enantiopure 4,5-Dihydroxy-2-Alkene Esters from Simple Allylic Alcohols
Aar, Marcel P. M. van,Thijs, Lambertus,Zwanenburg, Binne
, p. 9699 - 9712 (2007/10/02)
A general stereoselective synthesis of 4,5-dihydroxy-2-alkene esters is developed using the photo-induced rearrangement of α,β-epoxy diazomethyl ketones.Starting with readily available enantiopure allylic alcohols that contain a chiral center at C4, i.e. a protected secondary alcohol function, a neighboring stereogenic center is introduced by irradiation of the mentioned diazo ketones.The configuration of this newly introduced center is determined by the chiral inductor used in the Sharpless epoxidation of the allylic alcohol and therefore can be selected at will.
1,2-Asymmetric Induction in the Zwitterionic Claisen Rearrangement of Allylamines
Nubbemeyer, Udo
, p. 3773 - 3780 (2007/10/02)
A zwitterionic Claisen rearrangement has been developed for optically active N-allylpyrrolidines using a two-phase system.The inherent-1,2 asymmetric induction was investigated for the generation of a new C-C bond adjacent to a chiral C-O function.The reaction with acetyl chloride led to a small diastereomeric excess, whereas the rearrangement with propionyl chloride proceeded with a high simple and a high induced diastereoselection.The resulting γ,δ-unsaturated amides were cyclized to the corresponding optically active γ-butyrolactones, which are useful intermediates in natural product synthesis.
