24204-02-2

Upstream product

• 145471-65-4 (4aR,13bR,14aR)-4a-Benzenesulfonyl-13-(toluene-4-sulfonyl)-4,4a,7,8,13,13b,14,14a-octahydro-1H,3H-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-2,5-dione 
• 145471-66-5 C₃₄H₃₄N₂O₇S₂ 
• 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 
• 145471-64-3 4-oxo-3-(phenylsulfonyl)-12-(p-toluenesulfonyl)-1,4,6,7,12,12b-hexahydroindolo[2,3-a]quinolizine 
• 145471-67-6 C₂₈H₃₀N₂O₅S 
• 145471-63-2 4-oxo-3-(phenylsulfinyl)-12-(p-toluenesulfonyl)-1,4,6,7,12,12b-hexahydroindolo[2,3-a]quinolizine 
• 84406-16-6 3,3-Bis-phenylsulfanyl-2,3,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizin-4-one 
• 112274-06-3 C₂₁H₂₆N₂O₂ 
• 40088-10-6 (20α)-yohimban-17-one 
• 4942-85-2 1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-4-one 

Downstream Products

• 523-14-8 yohimban-17-one 

Relevant academic research and scientific papers

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

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.