54826-92-5Relevant academic research and scientific papers
Biomimetic Total Synthesis of Angiopterlactone B and Other Potential Natural Products
Kotammagari, Tharun K.,Gonnade, Rajesh G.,Bhattacharya, Asish K.
supporting information, p. 3564 - 3567 (2017/07/17)
A one-pot biomimetic synthesis of (-)-angiopterlactone B and its enantiomer (+)-angiopterlactone B has been accomplished via TBAF-catalyzed tandem ring contraction followed by oxa-Michael/Michael addition sequence. Comparison of specific optical rotations
Iridium-Catalyzed Dynamic Kinetic Isomerization: Expedient Synthesis of Carbohydrates from Achmatowicz Rearrangement Products
Wang, Hao-Yuan,Yang, Ka,Bennett, Scott R.,Guo, Sheng-Rong,Tang, Weiping
supporting information, p. 8756 - 8759 (2015/11/27)
A highly stereoselective dynamic kinetic isomerization of Achmatowicz rearrangement products was discovered. This new internal redox isomerization provided ready access to key intermediates for the enantio- and diastereoselective synthesis of a series of naturally occurring sugars. The nature of the de novo synthesis also enables the preparation of both enantiomers.
Synthesis of γ- and δ-lactone natural products by employing a trans-cis isomerization/lactonization strategy
Ono, Machiko,Kato, Keisuke,Akita, Hiroyuki
, p. 464 - 470 (2013/06/05)
Alkaline hydrolysis of 4-hydroxy- or/and 5-hydroxy-(2E)-alkenoate followed by acid treatment gave the corresponding (2E)-alkenoic acids which were subjected to lactone formation reaction without further purification. The crude acids were treated with 2,4,6-trichlorobenzoyl chloride in pyridine to afford ?-lactone or d-lactone, respectively, accompanied by trans-cis isomerization. By this procedure, (±)-(4,5)-trans-5-benzyloxy- 2-hexen-4-olide (90% overall yield), (S)-5-hydroxy-2-penten-4-olide (86% overall yield), (4S,5R)-5- hydroxy-2-hexen-4-olide (86% overall yield), (4R,5S)-5-hydroxy-2-hexen-4-olide (82% overall yield), (S)- parasorbic acid (58% overall yield) and natural product, (5R,7S)-7-hydroxy-2-octen-5-olide (euscapholide: 20% overall yield) were synthesized.
δ-Lactone formation from δ-hydroxy-trans-α,β-unsaturated carboxylic acids accompanied by trans-cis isomerization: synthesis of (-)-tetra-O-acetylosmundalin
Ono, Machiko,Zhao, Xi Ying,Shida, Yuki,Akita, Hiroyuki
, p. 10140 - 10148 (2008/02/13)
(±)-(4,5-anti)-4-Benzyloxy-5-hydroxy-(2E)-hexenoic acid 6 was subjected to δ-lactonization in the presence of 2,4,6-trichlorobenzoyl chloride and pyridine to give the α,β-unsaturated-δ-lactone congener (±)-7 (87% yield) accompanied by trans-cis isomerizat
A divergent approach to 3-azido-2,3,6-trideoxy-l-hexoses from rhamnal
Zhang, Guisheng,Shi, Lei,Liu, Qingfeng,Liu, Xiaobing,Li, Lu,Wang, Jingmei
, p. 3413 - 3416 (2008/02/10)
An alternative strategy has been developed for producing 3-azido-2,3,6-trideoxy-l-hexoses, protected forms of daunosamine, ristosamine, acosamine, and epi-daunosamine. This method involved BF3·OEt2-induced peroxidation of rhamnal to
A divergent strategy for constructing a sugar library containing 2,6-dideoxy sugars and uncommon sugars with 4-substitution
Zhang, Guisheng,Shi, Lei,Liu, Qingfeng,Wang, Jingmei,Li, Lu,Liu, Xiaobing
, p. 9705 - 9711 (2008/02/12)
A practical strategy has been developed for delivering 2,6-dideoxy sugars and uncommon sugars with 4-substitution. This strategy employed Ferrier rearrangement reaction and BF3·OEt2-induced peroxidation to construct key intermediates 2,3-unsaturated glycosides and α,β-unsaturated lactones from peracetyl rhamnal. After further derivatization, four uncommon sugars with 4-substitution and eight uncommon sugar units with 3,4-disubstitution were successfully synthesized.
A systematic strategy for preparation of uncommon sugars through enzymatic resolution and ring-closing metathesis
Zhu, Lizhi,Kedenburg, James P.,Xian, Ming,Wang, Peng George
, p. 811 - 813 (2007/10/03)
A systematic synthetic strategy has been developed for producing uncommon sugars. This method involved kinetic resolution allylic alcohol followed by ring-closing-metathesis (RCM) to generate optical pure lactones as the common precursors. After further d
A divergent synthesis of uncommon sugars from furanaldehyde
Zhu, Lizhi,Talukdar, Arindam,Zhang, Guisheng,Kedenburg, James P.,Wang, Peng George
, p. 1547 - 1550 (2007/10/03)
A practical synthetic strategy has been developed for producing uncommon sugars. This method employed kinetic enzymatic resolution of 1-(2-furyl)ethanol, and followed by NBS-mediated Achmatowicz rearrangement to construct α,β-unsaturated lactones. After further derivatization, five representative uncommon sugar units were successfully synthesized. Georg Thieme Verlag Stuttgart.
Stereoselective synthesis of the naturally occurring lactones (-)-osmundalactone and (-)-muricatacine using ring-closing metathesis
Carda, Miguel,Rodriguez, Santiago,Gonzalez, Florenci,Castillo, Encarnacion,Villanueva, Alicia,Marco, J. Alberto
, p. 2649 - 2655 (2007/10/03)
The stereoselective synthesis of the naturally occurring lactones osmundalactone (-)-1 and muricatacin (-)-2 is described, The key steps in each synthesis are the stereoselective addition of a Grignard reagent to a suitably protected α-hydroxy aldehyde an
The reaction of (4R,5R)- and (4S,5S)-4,5-epoxy-2(E)-hexenoates and secondary amines
Saotome,Ono,Akita
, p. 849 - 853 (2007/10/03)
A reaction of methyl (4R,5R)-4,5-epoxy-2(E)-hexenoate 1 with N-benzylmethylamine gave a diastereomerically pure methyl (4R,5R)-4,5-epoxy-(3S)-N-benzylmethylamino hexanoate 6 and methyl (4S,5R)-4-N-benzylmethylamino-5-hydroxy-2(E)-hexenoate 7. The former was chemoenzymatically converted to (-)-osmundalactone 11, which is an aglycone of osmundalin. On the other hand, the directly conjugated addition of dimethylamine to methyl (4S,5S)-4,5-epoxy-2(E)-hexenoate 1 followed by treatment with MeOH at 40°C exclusively provided methyl (4R,5S)-4-dimethylamino-5-hydroxy-2(E)-hexenoate 16, which was converted into L-(-)-forosamine 18.
