17322-84-8

Basic information

• Product Name: Pretazettine
• Synonyms: Pretazettine;(3S,13bS)-3,4,4aβ,5,6,6aβ-Hexahydro-3-methoxy-5-methyl-8H-[1,3]dioxolo[6,7][2]benzopyrano[3,4-c]indol-8β-ol;(6aβ)-6a-Deoxy-8β-hydroxytazettine;Isotazettine
• CAS NO: 17322-84-8
• Molecular Formula: C18H21NO5
• Molecular Weight: 331.366
• Mol File: 17322-84-8.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 499.6°Cat760mmHg
• Flash Point: 255.9°C
• Appearance: /
• Density: 1.41g/cm³
• Vapor Pressure: 8.45E-11mmHg at 25°C
• Refractive Index: 1.656
• CAS DataBase Reference: Pretazettine(CAS DataBase Reference)
• NIST Chemistry Reference: Pretazettine(17322-84-8)
• EPA Substance Registry System: Pretazettine(17322-84-8)

Safety Data

• Hazardous Substances Data: 17322-84-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C18H21NO5/c1-19-8-16-18(4-3-10(21-2)5-15(18)19)12-7-14-13(22-9-23-14)6-11(12)17(20)24-16/h3-4,6-7,10,15-17,20H,5,8-9H2,1-2H3/t10-,15+,16+,17?,18+/m1/s1

Upstream product

• 50-00-0 formaldehyd 
• 64-18-6 formic acid 
• 466-73-9 6-epihaemanthidine 
• 67-56-1 methanol 
• 74-88-4 methyl iodide 
• 73060-68-1 3α-hydroxy-3aβ-(2-hydroxymethyl-4,5-methylenedioxyphenyl)-6β-methoxy-N-methyl-2,3,6,7-tetrahydro-7aH-indole 
• 353246-56-7 6-hydroxyhaemanthamine 
• 353246-56-7 (3β,6β,11R,13β,19α)‐3‐methoxy‐1,2‐didehydrocrinan‐6,11‐diol 
• 78018-21-0 Methyl-6-brom-2,6-didesoxy-3-C-methyl-α-D-ribo-hexopyranosid 
• 135951-12-1 ((4S,5R)-2,2,4-Trimethyl-5-vinyl-[1,3]dioxolan-4-yl)-acetaldehyde 
• 135951-26-7 (3S,4R)-3-methyl-3,4-O-isopropylidene-5-hexenal dimethyl acetal 
• 259223-84-2 (4S,5S)-5-(2,2-Dimethoxy-ethyl)-2,2,5-trimethyl-[1,3]dioxolane-4-carbaldehyde 
• 259223-73-9 (3S,4R)-3,4-O-isopropylidene-3-methyl-5-(1,3-benzodioxol-5-yl)pentan-5-one-1-al dimethyl acetal 
• 259223-82-0 (E)-3-Benzo[1,3]dioxol-5-yl-3-[(4R,5S)-2,2,5-trimethyl-5-(2-oxo-ethyl)-[1,3]dioxolan-4-yl]-acrylic acid ethyl ester 

Downstream Products

• 507-79-9 tazettine 
• 1936-80-7 jonquailine 
• 1936-81-8 N-Desmethyl-3-epi-macronin 
• 1936-81-8 N-Desmethyl-macronin 
• 545-16-4 (4aS)-3t-methoxy-5-methyl-(4ar,13btC¹)-4,4a,5,6-tetrahydro-3H,8H-[1,3]dioxolo[4',5':6,7]isochromeno[3,4-c]indol-6at-ol 

Relevant articles and documents

Application of Electrocyclic Ring-Opening and Desymmetrizing Nucleophilic Trappings of meso-6,6-Dibromobicyclo[3.1.0]hexanes to Total Syntheses of Crinine and Haemanthamine Alkaloids

The thermally induced electrocyclic ring-opening of C2-symmetric (meso) 6,6-dibromobicyclo[3.1.0]hexanes such as 10 in the presence of the chiral, nonracemic 1°-amine 28 afforded a ca. 1:1 mixture of the diastereoisomeric and chromatographically separable 1-amino-2-bromo-2-cyclohexenes 37 (42%) and 38 (45%). Each of these was elaborated over 13 steps, including Suzuki-Miyaura cross-coupling, radical cyclization, and Pictet-Spengler reactions, into (-)- or (+)-crinane (1 or ent-1, respectively). Variations on these protocols were applied to the total syntheses of (+)- and (-)-11-hydroxyvattitine [(+)- and (-)-3], (+)- and (-)-bulbispermine [(+)- and (-)-4], (+)- and (-)-haemanthamine [(+)- and (-)-5], (+)- and (-)-pretazettine [(+)- and (-)-6], and (+)- and (-)-tazettine [(+)- and (-)-7] as well as (±)-hamayne [(±)-8] and (±)-apohaemanthamine [(±)-9]. A number of these alkaloids were synthesized for the first time.

First Asymmetric Total Syntheses of (+)-Crinamine, (-)-Haemanthidine, and (+)-Pretazettine

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Phenolic Oxidative Coupling with Hypervalent Iodine. A Synthesis of 6a-Epipretazettine

6a-Epipretazettine was synthesized in seven steps from piperonal and synephrine.Intramolecular, monophenolic, oxidative coupling of a functionalized benzylic acetal, employing benzene as oxidant, gave a spirodienone in 13 percent yield.Subsequent deprotection of the secondary amine was followed by spontaneous closure to a tetracyclic pyrrolidine possessing an all-cis ring fusion.This substance was reduced with diisobutylaluminum hydride, and the resulting alcohol was transformed, via methanolysis of the corresponding mesylate, to O-methyl-6a-epipretazettine.Acidic hydrolysis of the latter yielded 6a-epipretazettine, identical with material previously obtained by Danishefsky.