150736-85-9

Upstream product

• 94513-55-0 Dehydroryanodine 

Downstream Products

• 146036-45-5 10-O-(3-benzoyloxycarbamoylpropionyl)ryanodine 
• 148172-35-4 di-Cbz-guanidinoacetylryanodine 
• 148172-32-1 O_10eq-β-N,N'-bis-Cbz-guanidinopropionylryanodine 
• 6688-49-9 (+)-ryanodol 
• 106821-53-8 N,4-O,10-O,15-O-tetramethylryanodine 
• 97457-25-5 N,15-O-dimethylryanodine 
• 106821-49-2 N,6-O,15-O-trimethylryanodine 
• 106821-50-5 N,4-O,15-O-trimethylryanodine 
• 33068-29-0 24,25,26-tribromoryanodine 
• 106821-55-0 C₂₅H₃₅NO₁₁ 
• 146036-36-4 Cbz-glycylryanodine 
• 106821-47-0 N-benzylryanodine 
• 106821-48-1 N-butylryanodine 

Relevant academic research and scientific papers

Asymmetric Total Synthesis of (+)-Ryanodol and (+)-Ryanodine

(+)-Ryanodine (1) is the ester derivative of 1H-pyrrole-2-carboxylic acid and the complex terpenoid (+)-ryanodol (2), which possesses eleven contiguous stereogenic centers on the ABCDE-ring system. Compound 1 is known to be a potent modulator of intracellular calcium release channels, whereas the activity of 2 is significantly weaker. To chemically construct 1, the multiple oxygen functional groups must be installed on the fused pentacycle in stereoselective fashions and the extremely hindered C3-hydroxy group must be acylated in a site-selective manner. First, the total synthesis of 2 was accomplished by introducing the five stereocenters from the previously prepared enantiopure ABDE-ring 7. Stereoselective construction of the C3-secondary, C2- and C6-tertiary alcohols was achieved by three nucleophilic reactions. The C9- and C10-trisubstituted carbon centers were regio- and stereoselectively introduced by hydroboration/oxidation of the six-membered C-ring, which was formed by the ring-closing metathesis reaction. Direct esterification of the C3-alcohol with pyrrole-2-carboxylic acid proved unsuccessful; therefore, we developed a new, two-step protocol for attachment of the pyrrole moiety. The C3-hydroxy group was first converted into the less sterically cumbersome glycine ester, which was then transformed into the pyrrole ring through condensation with 1,3-bis(dimethylamino)allylium tetrafluoroborate. This procedure resulted in the first total synthesis of 1.

9,21-Didehydroryanodine: a New Principal Toxic Constituent of the Botanical Insecticide Ryania

A major insecticidal constituent of Ryania speciosa is isolated and characterized by n.m.r. and mass spectroscopy as the new alkaloid 9,21-didehydroryanodine (2); reduction of (2) with hydrogen (or tritium) gas yields both ryanodine (1) and 9-epiryanodine (3) (or their 9,21-3H analogues) in a 1 : 9 ratio.

Chemical conversion of ryanodol to ryanodine

Ryanodine (1) is a plant-derived natural product with powerful pharmacological and insecticidal action, and is a potent modulator of intracellular calcium release channels. Compound 1 possesses a 1H-pyrrole-2-carboxylate ester at the C3-position of heptahydroxylated terpenoid ryanodol (2). Whereas 2 was readily obtained from 1 by basic hydrolysis, 1 has never been synthesized from 2, due to the extreme difficulty in selectively introducing the bulky pyrrole moiety at the severely hindered C3-hydroxyl group of heptaol 2. Here we report chemical conversion of 2 to 1 for the first time. The derivatization was realized through the use of a new protective group strategy and the application of on-site construction of the pyrrole-2-carboxylate ester from the glycine ester and 1,3-bis(dimethylamino)allylium tetrafluoroborate.

Investigation of the constituents of Ryania Speciosa

Six new metabolites (2, 5-9) were isolated from the extracts of Ryania Speciosa Vahl.These compounds are closely related to ryanodine, the known insecticidal toxic alkaloid from this plant.