Stereospecific Synthesis of (+)-Muscarine from D-Glucose, Suitable for Preparation of 5-Substituted Analogues

1998 ◽  
Vol 63 (10) ◽  
pp. 1522-1527 ◽  
Author(s):  
Velimir Popsavin ◽  
Ostoja Beric ◽  
Ljubica Radic ◽  
Mirjana Popsavin ◽  
Vera Cirin-Novta ◽  
...  
Keyword(s):  
Catalytic Hydrogenation ◽  
Mitsunobu Reaction ◽  
Stereospecific Synthesis ◽  
Key Steps ◽  
Stereospecific Cyclization

A stereospecific synthesis of (+)-muscarine iodide (1) has been achieved starting from D-glucose as a chiral precursor. The key steps of the synthesis involved a stereospecific cyclization of 3,5-di-O-mesyl derivative 3 into the 2,5-anhydride 4, the stereospecific catalytic hydrogenation of unsaturated derivative 6, and the C-4 epimerization of alcohol 12 by Mitsunobu reaction.

Exploratory synthetic investigations related to 12a-deoxypillaromycinone

2002 ◽  
Vol 80 (6) ◽  
pp. 728-738 ◽  
Author(s):  
Lan Wang ◽  
Sanath K Meegalla ◽  
Cheng-Lin Fang ◽  
Nicholas Taylor ◽  
Russell Rodrigo
Keyword(s):  
Double Bond ◽  
Catalytic Hydrogenation ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Step Procedure ◽  
Key Steps

Furfural is converted to suitably substituted AB synthon 21 for 12a-deoxypillaromycinone in 10 steps by a sequence involving the following key steps: intramolecular Diels-Alder reaction of a furan, 5-endo-trig cleavage of the oxabicyclo adducts 18, and catalytic hydrogenation of the double bond of a tetrasubstituted enone to produce 19. Enones 21a and 21b obtained by dehydrogenation of 19a and 19b, respectively, are then annulated with ethyl 2-methoxy-6-methylbenzoate in a four-step procedure to generate tetracyclic products 25 in 14 steps from furfural.

Stereospecific Synthesis of (-)-allo-Muscarine from D-Glucose: Novel Routes to the Key Chiral Synthon

1997 ◽  
Vol 62 (5) ◽  
pp. 809-815 ◽  
Author(s):  
Velimir Popsavin ◽  
Ostoja Beric ◽  
Mirjana Popsavin ◽  
János Csanádi ◽  
Stevan Lajšic ◽  
...  
Keyword(s):  
Mitsunobu Reaction ◽  
Stereospecific Synthesis ◽  
Novel Synthesis ◽  
Derivatives Of ◽  
Chiral Synthon ◽  
Ethylene Acetal

The key chiral synthon in a novel synthesis of (-)-allo-muscarine from D-glucose has been prepared by three independent routes. The most efficient one includes a four-step conversion via the 4-O-benzoyl derivatives of starting 2,5-anhydro-3,5-di-O-methanesulfonyl-L-idose ethylene acetal (2a) into 2,5-anhydro-3,6-dideoxy-L-lyxo-hexose ethylene acetal (4b). The intermediate 4b was efficiently converted into the chiral synthon 2,5-anhydro-4-O-benzoyl-3,6-dideoxy-L-arabino-hexose (4c) by Mitsunobu reaction.

A Stereospecific Synthesis of L-Desosamine

1974 ◽  
Vol 52 (1) ◽  
pp. 122-124 ◽  
Author(s):  
Hans H. Baer ◽  
Chung-Wai Chiu
Keyword(s):  
Acid Hydrolysis ◽  
Nitro Group ◽  
Catalytic Hydrogenation ◽  
Glycosidic Bond ◽  
Stereospecific Synthesis ◽  
Borohydride Reduction ◽  
Amino Glycoside ◽  
Hydrolysis Of

L-Desosamine (3,4,6-trideoxy-3-dimethylamino-L-xylo-hexose), the enantiomer of a widely distributed antibiotics component, was synthesized by borohydride reduction of methyl 3,4,6-trideoxy-3-nitro-α-L-erythro-hex-3-enopyranoside followed by catalytic hydrogenation of the nitro group, N,N-dimethylation of the resulting saturated amino glycoside, and acid hydrolysis of the glycosidic bond.

Enantioselective Total Synthesis of Ligraminol D and Ligraminol E

Synlett ◽  
2019 ◽  
Vol 30 (20) ◽  
pp. 2285-2289
Author(s):  
Baliram B. Mane ◽  
D. D. Kumbhar ◽  
Suresh B. Waghmode
Keyword(s):  
Total Synthesis ◽  
Mitsunobu Reaction ◽  
Bioactive Constituents ◽  
Ongoing Research ◽  
Total Syntheses ◽  
Enantioselective Total Synthesis ◽  
Key Steps

As a part of our ongoing research on the synthesis of bioactive constituents or molecules by using an organocatalytic approach, enantioselective total syntheses of ligraminol D and ligraminol E were achieved starting from a commercially available nonchiral aldehyde. Key steps in this synthesis were an asymmetric α-aminoxylation of an aldehyde and a Mitsunobu reaction.

Stereospecific synthesis of isomeric 4-substituted 9-(2,3-dihydroxybutyl)adenines

1982 ◽  
Vol 47 (1) ◽  
pp. 173-189 ◽  
Author(s):  
Antonín Holý
Keyword(s):  
Acid Hydrolysis ◽  
Sodium Borohydride ◽  
Sodium Salt ◽  
Catalytic Hydrogenation ◽  
Sodium Azide ◽  
Sodium Iodide ◽  
Stereospecific Synthesis ◽  
Isopropylidene Derivative

Reduction of ethyl 2,3-O-isopropylidene-D-tartrate with sodium borohydride afforded (4S, 5S)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol (Va) which was benzoylated to give monobenzoyl derivative Vd and further transformed into p-toluensulfonyl derivative Ve. Reaction of the compound Ve with sodium salt of adenine followed by methanolysis gave 2,3-O-isopropylidene derivative Vf which on acid hydrolysis afforded 9-(2S, 3S)-(2,3,4-trihydroxybutyl)adenine (Ia). The enantiomer IIa was obtained from 3,4-O-isopropylidene-D-mannitol via (4R, 5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol (VIa) using the same procedure. Reaction of compounds Vf and VIf with p-toluenesulfonyl chloride afforded 4-O-p-toluenesulfonyl derivatives Vg and VIg. These compounds were also obtained from Va and VIa via di-p-toluenesulfonyl derivatives Vc and VIc by reaction with sodium salt of adenine. Treatment of compounds Vg and VIg with sodium iodide gave 4-iodo derivatives Vh and VIh which on reaction with tri-n-butyltin hydride, followed by acid hydrolysis, afforded enantiomeric threo-2,3-dihydroxybutyl derivatives Ib andIIb. Compounds Vg and VIg on treatment with sodium azide, subsequent catalytic hydrogenation of the intermediates Vj and VIj and acid hydrolysis afforded enantiomeric threo-9-(4-amino-2,3-dihydroxybutyl)adenines (Ic,IIc).

A new and efficient enantioselective synthesis of both enantiomers of the calcium channel blocker bepridil

2017 ◽  
Vol 41 (2) ◽  
pp. 824-829 ◽  
Author(s):  
Mohammad Mujahid ◽  
Jambu Subramanian ◽  
Viswanadh Nalla ◽  
Murugesan Sasikumar ◽  
Sunita Sharad Kunte ◽  
...  
Keyword(s):  
Calcium Channel ◽  
Calcium Channel Blocker ◽  
Kinetic Resolution ◽  
Channel Blocker ◽  
Enantioselective Synthesis ◽  
Mitsunobu Reaction ◽  
Hydrolytic Kinetic Resolution ◽  
Key Steps

We report a simple enantioselective synthesis of bepridil enantiomers employing hydrolytic kinetic resolution and the Mitsunobu reaction as key steps.

One-Pot and Stereospecific Synthesis of cis-1,2-Diazides via Mitsunobu Reaction of Epoxides.

ChemInform ◽  
2003 ◽  
Vol 34 (10) ◽  
Author(s):  
Sueleyman Goeksu ◽  
Hasan Secen ◽  
Yasar Suetbeyaz
Keyword(s):  
Mitsunobu Reaction ◽  
Stereospecific Synthesis ◽  
One Pot

scholarly journals Ultrasonicated Synthesis ofN-Benzyl-2,3-substituted Morpholines, via the Mitsunobu Diol Cyclisation

2010 ◽  
Vol 7 (4) ◽  
pp. 1184-1189
Author(s):  
B. Jayachandra Reddy ◽  
M. C. Somasekhara Reddy
Keyword(s):  
Column Chromatography ◽  
Good Yield ◽  
Mitsunobu Reaction ◽  
Microwave Assisted ◽  
Chemical Studies ◽  
Key Steps

A facile five step synthesis ofN-benzyl-2,3-substituted morpholines (i-iii) was performed. The key steps were microwave assisted Friedel-crafts acylation and diol cyclization carried out via an ultra sonication of Mitsunobu reaction using DEAD (diethylazodicarboxylate), TPP in THF for 1 h. The morpholine products were generated as diasteriomers (iiandiii) which has been separated by the column chromatography to good yield. The structure of compounds (i-iii) has been characterized by the spectral and chemical studies.

ChemInform Abstract: Stereospecific Synthesis of Secondary Amines by the Mitsunobu Reaction.

ChemInform ◽  
2010 ◽  
Vol 22 (18) ◽  
pp. no-no
Author(s):  
M. L. EDWARDS ◽  
D. M. STEMERICK ◽  
J. R. MCCARTHY
Keyword(s):  
Mitsunobu Reaction ◽  
Secondary Amines ◽  
Stereospecific Synthesis
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