A Palladium(II)-Catalyzed Construction of .alpha.-Methylene-.gamma.-butyrolactones in Optically Active Form. Total Synthesis of (-)-Methylenolactocin

1995 ◽  
Vol 60 (4) ◽  
pp. 1087-1089 ◽  
Author(s):  
Guoxin Zhu ◽  
Xiyan Lu
Keyword(s):  
Total Synthesis ◽  
Active Form ◽  
Optically Active

Isolation, structure, and synthesis of chenopodanol and the absolute configuration of chenopodene and chenopodanol

1997 ◽  
Vol 75 (6) ◽  
pp. 634-640 ◽  
Author(s):  
Motoo Tori ◽  
Tomonobu Hamaguchi ◽  
Mamiko Aoki ◽  
Masakazu Sono ◽  
Yoshinori Asakawa
Keyword(s):  
Total Synthesis ◽  
Absolute Configuration ◽  
Active Form ◽  
Optically Active ◽  
Spectroscopic Techniques ◽  
The Absolute

(−)-Chenopodanol (2) has been isolated from the liverwort Marchantiachenopoda and its structure determined by spectroscopic techniques as well as by total synthesis. Chenopodene (1) has also been synthesized in an optically active form, resulting in revision of the originally assigned absolute configuration. Keywords: chenopodanol, chenopodene, liverwort, Marchantiachenopoda, sesquiterpene.

Total synthesis of zizaane sesquiterpenes: (−)-khusimone, (+)-zizanoic acid, and (−)-epizizanoic acid

1982 ◽  
Vol 60 (9) ◽  
pp. 1081-1091 ◽  
Author(s):  
Hsing-Jang Liu ◽  
Wing Hong Chan
Keyword(s):  
Total Synthesis ◽  
Ammonium Salt ◽  
Active Form ◽  
Optically Active ◽  
Camphorsulfonic Acid

Three sesquiterpenes of the zizaane family, khusimone (1), epizizanoic acid (3), and zizanoic acid (2) have been synthesized in optically active form from the ammonium salt of (−)-l-10-camphorsulfonic acid in sixteen, nineteen, and twenty steps respectively.

Phenserine, a Novel Anticholinesterase Related to Physostigmine: Total Synthesis and Biological Properties

1996 ◽  
Vol 49 (2) ◽  
pp. 171 ◽  
Author(s):  
A Brossi ◽  
XF Pei ◽  
NH Greig
Keyword(s):  
Amyloid Precursor Protein ◽  
Total Synthesis ◽  
Active Form ◽  
Biological Properties ◽  
Optically Active ◽  
National Institutes Of Health ◽  
Drug Candidate ◽  
Experimental Animals ◽  
Β Amyloid ◽  
Potential Use

Phenserine, the phenylcarbamate analogue of physostigmine , is a drug candidate of potential use for treating Alzheimer's disease. Phenserine inhibits acetylcholinesterase selectively, improves memory dramatically in experimental animals without toxicity, and reduces the production of β-amyloid precursor protein, the source of the Alzheimer's toxin β-amyloid. Phenserine was made from physostigmine in two steps, and it can be prepared in the required optically active form by total synthesis. For this purpose, the oxindole route developed by Julian in his total synthesis of physostigmine was vastly improved. Details of this work performed at the National Institutes of Health and at Institutions sponsored by this agency are presented herein.

The total synthesis of optically active annotinine

1969 ◽  
Vol 47 (3) ◽  
pp. 433-444 ◽  
Author(s):  
K. Wiesner ◽  
Lizzie Poon ◽  
I. Jirkovský ◽  
M. Fishman
Keyword(s):  
Total Synthesis ◽  
Active Form ◽  
Optically Active ◽  
Lycopodium Alkaloid

The total synthesis of the first Lycopodium alkaloid annotinine in the optically active form is described. The key step in this synthesis was the photochemical addition of allene to the tricyclic vinylogous imide (3) which yielded the photoadduct (6).

Synthesis of Optically Active Hydroxyalkyl Cycloheptatrienes: A Key Step in the Total Synthesis of 6,11-Methylene-LXB4

Synlett ◽  
2020 ◽  
Vol 32 (01) ◽  
pp. 45-50
Author(s):  
Udo Nubbemeyer ◽  
Analuisa Nava ◽  
Lukas Trippe ◽  
Andrea Frank ◽  
Lars Andernach ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Total Synthesis ◽  
Structure Elucidation ◽  
Butyl Ester ◽  
Optically Active ◽  
Chiral Hplc ◽  
Reaction Conditions ◽  
Acid Product ◽  
Tert Butyl ◽  
Nabh4 Reduction

AbstractStarting from methyl cycloheptatrienyl-1-carboxylate, 6-acylation was successfully achieved employing glutaryl chloride in the presence of AlCl3 under controlled reaction conditions to furnish keto carboxylic acid product. After protection of this keto carboxylic acid as tert-butyl ester, reagent-controlled enantioselective reductions delivered configuration-defined methyl-6-hydroxylalkyl cycloheptatriene-1-carboxylates with up to 80% ee. Whereas simple NaBH4 reduction of the keto carboxylic acid and subsequent lactonization afforded a methyl-6-tetrahydropyranonyl cycloheptatriene-1-carboxylate. Resolution using chiral HPLC delivered the product enantiomers with up to >99% ee Finally, ECD analyses enabled structure elucidation. The products are used as key intermediates in enantioselective 6,11-methylene-lipoxin B4 syntheses.

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