30343-72-7

Usage

Uses

1. Used in Pharmaceutical Industry:
(3S,4'S,9aβ,9''aβ)-6α,6''α-Di-(3-furyl)-1,6,7,8,9,9a,1'',6'',7'',8'',9'',9a''-dodecahydro-9β,9''β-dimethyldispiro[2H-quinolizine-3(4H),2'(3'H)-thiophene-4'(5'H),3''(4''H)-[2H]quinolizine] is used as a pharmaceutical compound for its potential therapeutic applications. The unique molecular structure and properties of this alkaloid make it a promising candidate for the development of new drugs and therapies.
2. Used in Chemical Research:
(3S,4'S,9aβ,9''aβ)-6α,6''α-Di-(3-furyl)-1,6,7,8,9,9a,1'',6'',7'',8'',9'',9a''-dodecahydro-9β,9''β-dimethyldispiro[2H-quinolizine-3(4H),2'(3'H)-thiophene-4'(5'H),3''(4''H)-[2H]quinolizine] is also used in chemical research for studying its properties, reactivity, and potential applications in various chemical processes. Its complex structure and unique features make it an interesting subject for further investigation and understanding.
3. Used in Material Science:
The unique structural features of (3S,4'S,9aβ,9''aβ)-6α,6''α-Di-(3-furyl)-1,6,7,8,9,9a,1'',6'',7'',8'',9'',9a''-dodecahydro-9β,9''β-dimethyldispiro[2H-quinolizine-3(4H),2'(3'H)-thiophene-4'(5'H),3''(4''H)-[2H]quinolizine] may have potential applications in material science, particularly in the development of new materials with specific properties and functions.

References

Achmatowicz, Bellen., Tetrahedron Lett., 1121 (1962)Achmatowicz, Wrobel., ibid, 129,927 (1964)

Upstream product

• 547-65-9 α-methylene-γ-butyrolactone 
• 75420-44-9 (-)-(3R)-methyl-4-penten-1-ol 
• 55254-35-8 (R)-3-methyl-dihydro-furan-2-one 

Relevant academic research and scientific papers

Total Synthesis of Unsymmetrically Oxidized Nuphar Thioalkaloids via Copper-Catalyzed Thiolane Assembly

An asymmetric total synthesis of (+)-6-hydroxythiobinupharidine (1b) and (-)-6-hydroxythionuphlutine (2b), a set of hemiaminal containing dimeric sesquiterpenes isolated from yellow water lilies of the Nuphar genus, is described. The central bis-spirocyclic tetrahydrothiophene ring was forged through the Stevens rearrangement of a sulfonium ylide, generated in situ from the coupling of a copper-carbene with a spirocyclic thietane. This strategy diverges both from the proposed biosynthesis1 and previous syntheses of this family of alkaloids,2,3 all of which employ dimerization of symmetric monomers to form the aforementioned thiaspirane. The coupling of unsymmetrical monomers allowed access to the unsymmetrically oxidized product 2b for the first time.

Total Syntheses and Biological Evaluation of Both Enantiomers of Several Hydroxylated Dimeric Nuphar Alkaloids

Herein, we describe the first total syntheses of five members of the dimeric nuphar alkaloids: (+)-6,6′-dihydroxythiobinupharidine (+)-1a, (+)-6-hydroxythiobinupharidine (+)-1-b, (-)-6,6′-dihydroxythionuphlutine (-)-2-a, (-)-6,6′-dihydroxyneothiobinupharidine (-)-3a, and (+)-6,6′-dihydroxyneothionuphlutine (+)-4-a. The latter two have not been found in nature. We have also made each of their enantiomers (-)-1a-b, (+)-2a, (+)-3a, and (-)-4a. The key step in these syntheses was the dimerization of an α-aminonitrile (a hydrolytically stable surrogate for its corresponding hemiaminal) with chiral Lewis acid complexes. We have also reassigned the literature structures of (+)-1-a-1b - for those instances in which the NMR spectra were obtained in CD3OD - to their corresponding CD3O-adducts. Our efforts provide for the first time apoptosis data for (-)-3a, (+)-4a, and all five non-natural enantiomers prepared. The data indicate high apoptotic activity regardless of the enantiomer or relative stereochemical configuration at C7 and C7′. Nuphars are speedy killers: For the first time several of the hydroxylated dimeric nuphar alkaloids and their unnatural enantiomers have been synthesized. First-ever apoptosis data for many of these compounds is provided.

Synthesis of (-)-neothiobinupharidine

An eight step, asymmetric synthesis of a dimeric thiaspirane nuphar alkaloid from 3-methyl-2-cyclo-pentenone is reported. The brevity of the route relies on a useful procedure for tandem reductive allylation of cyclopentenones, as well as the minimization of redox manipulations and other functional group interconversions. The distribution of products that arise from spontaneous dimerization points to a more complex biosynthesis.

Crude drugs from aquatic plants. VI. On the alkaloid constituents of Chinese Nupharis Rhizoma, the dried rhizoma of Nuphar pumilum (TIMM.) DC. (Nymphaceae) : Structures and rearrangement reaction of thiohemiaminal type nuphar alkaloids

From Chinese Nupharis Rhizoma, the dried rhizoma of Nuphar pumilum (TIMM.) DC. (Nymphaceae), four thiohemiaminal type nuphar alkaloids with potent immuno-suppressive activity, 6-hydroxythiobinupharidine, 6,6′-dihydroxythiobinupharidine, 6-hydroxythionuphlutine B, 6′-hydroxythionuphlutine B, have been isolated together with nine inactive nuphar alkaloids. The configurations of the 6- and 6′-hydroxyl groups in those thiohemiaminal type nuphar alkaloids were confirmed on the basis of their 2D-NMR analysis. During the course of chemical elucidation of those thiaspirane type dimeric sesquiterpene alkaloids, new rearrangement reaction of the thiaspirane ring in thiohemiaminal type alkaloids with 6-hydroxyl group was found and the reaction pathway was discussed. By using this rearrangement reaction, 6-hydroxythionuphlutine B was chemically related with 6-hydroxythiobinupharidine, so that the absolute stereostructures of thionuphlutine B and its related compounds such as 6-hydroxythionuphlutine B, 6′-hydroxythionuphlutine B, and thionuphlutine B β-sulfoxide, were characterized.