549-91-7

Usage

Uses

Used in Pharmaceutical Industry:
(2R)-3β-Ethyl-1,3,4,6,7,11bβ-hexahydro-9,10-dimethoxy-2H-benzo[a]quinolizine-2α-acetaldehyde is used as an active pharmaceutical ingredient for the development of new drugs. Its unique chemical structure and optical activity make it a promising candidate for various therapeutic applications, including the treatment of various diseases and disorders.
Used in Chemical Research:
(2R)-3β-Ethyl-1,3,4,6,7,11bβ-hexahydro-9,10-dimethoxy-2H-benzo[a]quinolizine-2α-acetaldehyde is also used as a research tool in the field of organic chemistry, particularly for studying the synthesis, structure, and properties of complex organic molecules. Its unique characteristics and reactivity can provide valuable insights into the development of new synthetic methods and the understanding of molecular interactions.
Used in Analytical Chemistry:
(2R)-3β-Ethyl-1,3,4,6,7,11bβ-hexahydro-9,10-dimethoxy-2H-benzo[a]quinolizine-2α-acetaldehyde can be employed as a reference compound in analytical chemistry for the development and validation of new analytical methods, such as chromatography, spectroscopy, and other techniques. Its distinct optical activity and characteristic absorption maxima in the ultraviolet spectrum make it a suitable candidate for these applications.

References

Battersby, Davidson, Harper.,J. Chem. Soc., 1744 (1959) Battersby, Harper., ibid, 1748 (1959) Synthesis: Santay, Toke, Kolonits., J. Org. Chem., 31, 1447 (1966)

Upstream product

• 1361016-14-9 C₁₉H₂₅NO₃ 
• 3332-90-9 (+/-)-(3c-ethyl-9,10-dimethoxy-(11br)-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2t-yl)-acetic acid methyl ester 
• 1357385-48-8 {(2R,3R,11bS)-2-[2-(benzyloxy)ethyl]-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-yl}methanol 
• 1357385-46-6 methyl (2R,3R,11bS)-2-[2-(benzyloxy)ethyl]-9,10-dimethoxy-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinoline-3-carboxylate 
• 1361016-21-8 C₁₉H₂₇NO₄ 
• 123001-21-8 (+)-(4S,5R)-4-(2-Benzyloxyethyl)-5-ethyl-3,4,5,6-tetrahydro-2-pyrone 
• 1325690-29-6 C₁₉H₂₆O₆ 
• 1325690-27-4 C₁₅H₁₈O₅ 
• 122937-65-9 (-)-(2R,3R,11bS)-2-(2-Benzyloxyethyl)-3-ethyl-1,2,3,4,6,7-hexahydro-9,10-dimethoxy-11bH-benzoquinolizidine 
• 7344-78-7 (-)-protoemetinol 
• 98062-25-0 tert-butyl N-[2-(3,4-dimethoxyphenyl)ethyl]carbamate 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 

Downstream Products

• 522-99-6 isoemetine 
• 483-18-1 emetine 

Relevant academic research and scientific papers

A Chiral Pentenolide-Based Unified Strategy toward Dihydrocorynantheal, Dihydrocorynantheol, Protoemetine, Protoemetinol, and Yohimbane

An organocatalytic cross-aldol reaction of formaldehyde (formalin) with alkyl aldehydes, followed by the Z-selective Horner-Wadsworth-Emmons (HWE) reaction and immediate lactonization, afforded γ-alkylated pentenolides in good overall yields and excellent

Concise total synthesis of dihydrocorynanthenol, protoemetinol, protoemetine, 3-epi-protoemetinol and emetine

A concise asymmetric assembly of secologanine tryptamine and dopamine alkaloids by means of a one-pot three-component cascade reaction methodology is disclosed. This is demonstrated by the expeditious total syntheses of (-)-dihydrocorynanthenol, (-)-protoemetinol, (-)-protoemetine, (-)-3-epi-protoemetinol, and emetine (3-6 steps). The biomimetic synthetic strategy involved the following key steps: (i) One-pot three-component highly enantioselective catalytic Michael/Pictet-Spengler/lactamization cascade reactions; (ii) One-pot tandem Swern oxidation/Wittig sequences; (iii) One-pot tandem hydrogenation sequences. Copyright

Organocatalytic approach for the syntheses of corynantheidol, dihydrocorynantheol, protoemetinol, protoemetine, and mitragynine

O-Trimethylsilyl (TMS)-protected diphenylprolinol-catalyzed Michael addition of a functionalized alkylidene malonate and n-butanal affords an aldehyde. This adduct can serve as the common intermediate for the assembly of secologanin tryptamine and dopamin

A stereodivergent strategy for the preparation of corynantheine and ipecac alkaloids, their epimers, and analogues: Efficient total synthesis of (-)-dihydrocorynantheol, (-)-corynantheol, (-)-protoemetinol, (-)-corynantheal, (-)-protoemetine, and related

Here we present a general and common catalytic asymmetric strategy for the total and formal synthesis of a broad number of optically active natural products from the corynantheine and ipecac alkaloid families, for example, indolo[2,3-a]- and benzo[a]quino

Asymmetric Total Synthesis of (-)-Protoemetinol, (-)-Protoemetine, (-)-Emetine, and (-)-Tubulosine by Highly Stereocontrolled Radical Cyclisations

Both enantiomers of the menthyl half-esters (10) and (23) of ethylmalonic acid were converted into (+)-(4S,5R)-4-(2-benzyloxyethyl)-5-ethyl-3,4,5,6-tetrahydro-2-pyrone (18).A mixture of the trans-(18) and cis-lactones (19) in a ratio of ca. 4:1 was prepared by way of radical cyclisation of the (E)-α,β-unsaturated esters (16), while the former (18) was synthesised with high stereoselection by the cyclisation of the (Z)-esters (26).The lactone (18) was enantioselectively transformed into (-)-protoemetinol (5) and (-)-protoemetine (4), correlated to (-)-emetine (1) and (-)-tubulosine (3).

TOTAL SYNTHESIS OF MONOTERPENOID ISOQUINOLINE ALKALOIDS

A novel analogue (3) of dihydrosecologanin aglucone has been synthesised via a substituted cyclopentenolone and converted into (+/-)-protoemetine (10) amd related Ipecac alkaloids.

SYNTHESIS OF THE IPECAC ALKALOIDS FROM NORCAMPHOR

A general route to the Ipecac Alkaloids from norcamphor (8) has been developed.Alkylation of the bicyclic lactone (9), obtained from norcamphor (8), gave the endo-isomer (10), exlusively, which was converted in four steps to the key intermediate (14).The