523-14-8

Usage

InChI:InChI=1/C19H22N2O/c22-14-6-5-12-11-21-8-7-16-15-3-1-2-4-17(15)20-19(16)18(21)10-13(12)9-14/h1-4,12-13,18,20H,5-11H2

Upstream product

• 158146-68-0 17β-hydroxy-18,19-didehydroyohimbane 
• 158146-59-9 2,2-Dimethyl-propionic acid (4aS,6S,7R,8aR)-7-hydroxy-2-[2-(1H-indol-3-yl)-ethyl]-3-oxo-decahydro-isoquinolin-6-yl ester 
• 158146-60-2 2,2-Dimethyl-propionic acid (4aS,6S,8aS)-2-[2-(1H-indol-3-yl)-ethyl]-3-oxo-1,2,3,4,4a,5,6,8a-octahydro-isoquinolin-6-yl ester 
• 158146-67-9 17β-(trimethylacetoxy)-18,19-didehydroyohimbane 
• 114926-72-6 (S)-(-)-1-<(5-metoxy-1,4-cyclohexadienyl)methyl>-1,2,3,4-tetrahydro-β-carboline 
• 114926-76-0 15(S)-methoxyyohimban-17-ol 
• 114926-75-9 15(R)-methoxyyohimban-17-ol 
• 59904-68-6 (+/-)-yohimbenone 
• 145471-62-1 4-oxo-3,3-bis(phenylthio)-12-(p-toluenesulfonyl)-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine 
• 40088-10-6 (20α)-yohimban-17-one 
• 113542-21-5 (E)-7-Trimethylsilanylmethyl-octa-3,7-dienylamine 
• 54725-64-3 18,19-didehydroyohimban-17-one 
• 2671-57-0 (+)-yohimbinone 
• 114926-77-1 (4aR,13bS)-3,4,4a,5,8,13,13b,14-octahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinolin-2(7H)-one 

Downstream Products

• 2270-72-6 Dihydrocorynantheol 

Relevant academic research and scientific papers

Symmetry-driven synthesis of indole alkaloids: Asymmetric total synthesis of (+)-yohimbine, (-)-yohimbone, (-)-yohimbane, and (+)-alloyohimbane

Total asymmetric syntheses of the target alkaloids are reported. The syntheses involve the preparation of enantiomerically pure (S,S)-1,3,3a,4,7,7a-hexahydro-2(H)-inden-2-one 7 and its meso isomer 5. Each ketone is then converted into a ring-expanded lactam using an oxaziridine synthesis/rearrangement protocol. The applications of Bischler-Napieralski ring constructions along with appropriate functional group transformations afford enantiomerically enriched alloyohimbane or yohimbane from the meso-or C2-symmetric ketones, respectively. A cis-5,6-diacetoxy compound (18) derived from the (S,S)-ketone served as the starting material for the total syntheses of the more highly functionalized alkaloids. Accordingly, a site-specific insertion of the indole-containing side chain was accomplished via stereoselective formation of an oxaziridine followed by its stereospecific rearrangement. The selectivity of this sequence allowed for the differentiation of alcohols at C-17 and C-18 (yohimbine numbering) and the synthesis of Δ18,19-yohimbone. This α,β-unsaturated ketone was converted into either (-)-yohimbone or (+)-yohimbine using standard chemistry.

A New ABCDE> Cycloaddition Strategy for the Approach to Yohimbe Alkaloids: Stereoselective Synthesis of (+/-)-3-epi-allo-Yohimbone

Diels-Alder cycloaddition between lactam-sulfone 9 and diene 10 led to adducts 11 + 12 (30:1, respectively).Compound 11 has been converted in 4 steps into (+/-)-3-epi-allo-yohimbone 16.Key words: Diels-Alder cycloaddition, Yohimbe alkaloids, (+/-)-3-epi-a

Chiral and Achiral Formamidines in Synthesis. The First Asymmetric Route to (-)-Yohimbone and an Efficient Total Synthesis of (+/-)-Yohimbone

An asymmetric synthesis of (-)-yohimbone from chiral formamidines is presented.The synthetic pathway intercepts a previously reported route to yohimbenone (6) reported by Winterfeldt.An investigation of the -rearrangement involving iminium salts 8 an

Iminium Ions as Initiators and Allylsilanes as Terminators in Polyolefin Cyclizations: Total Synthesis of (+/-)-Yohimbone via A Vinylogous Aminomethano Desilylation

A syntyheses of (+/-)-yohimbone has been realized via a concerted iminium ion-induced polyolefin cyclization terminated by an allylsilane.

GENERAL METHODS OF SYNTHESIS OF INDOLE ALKALOIDS - 14. SHORT ROUTES OF CONSTRUCTION OF YOHIMBOID AND AJMALICINOID ALKALOID SYSTEMS AND THEIR 13C NUCLEAR MAGNETIC RESONANCE SPECTRAL ANALYSIS.

Conceptually new schemes of synthesis of indole alkaloids are introduced. The yohimboid ring system is constructed by the sequential treatment of 1-tryptophyl-3-( beta -ketobutyl)pyridinium bromide with base and acid. Hydrogenation of the product yields d,l-pseudoyohimbone. The ajmalicinoid ring system is formed by the exposure of 1-tryptophyl-3-acetylpyridinium bromide to sodio dimethyl malonate and then to acid, followed by hydrogenation. Subsequent reduction and dehydration of the products lead to the racemates of the alkaloids tetrahydroalstonine and akuammigine as well as isomers of ajmalicine. Shifts of specific carbons are found to be of stereochemically diagnostic value.