87946-74-5

Basic information

• Product Name: Specionin
• Synonyms: (-)-Specionin;4-Hydroxybenzoic acid (1aS,1bα,5aα,6aβ)-2β,4α-diethoxyoctahydro-1aβ-(hydroxymethyl)oxireno[4,5]cyclopenta[1,2-c]pyran-6α-yl ester;Specionin
• CAS NO: 87946-74-5
• Molecular Formula: C₂₀H₂₆O₈
• Molecular Weight: 394.41564
• Mol File: 87946-74-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Specionin(CAS DataBase Reference)
• NIST Chemistry Reference: Specionin(87946-74-5)
• EPA Substance Registry System: Specionin(87946-74-5)

Safety Data

• Hazardous Substances Data: 87946-74-5(Hazardous Substances Data)

Upstream product

• 109519-08-6 4-Benzyloxy-benzoic acid (1bR,5aS,6R)-2,4-diethoxy-1a-hydroxymethyl-octahydro-1,3-dioxa-cyclopropa[a]inden-6-yl ester 
• 109519-08-6 4-Benzyloxy-benzoic acid (1aS,1bS,2S,4S,5aR,6S,6aS)-2,4-diethoxy-1a-hydroxymethyl-octahydro-1,3-dioxa-cyclopropa[a]inden-6-yl ester 
• 114972-77-9 (3aR,5R,6S,6aS)-5,6-Bis-benzyloxy-3,3a,4,5,6,6a-hexahydro-pentalene-1-carbaldehyde 
• 114972-75-7 (3aR,5R,6S,6aR)-5,6-Bis-benzyloxy-hexahydro-pentalen-1-one 
• 109519-11-1 4-Benzyloxy-benzoic acid (1aS,1bS,2R,5aR,6S,6aS)-1a-(tert-butyl-dimethyl-silanyloxymethyl)-2,4-diethoxy-octahydro-1,3-dioxa-cyclopropa[a]inden-6-yl ester 
• 109669-25-2 6-O-benzyl-10-O-t-butyldimethylsilyl catalposide, β ethyl acetal 
• 109519-08-6 4-Benzyloxy-benzoic acid (1aS,1bS,2R,4S,5aR,6S,6aS)-2,4-diethoxy-1a-hydroxymethyl-octahydro-1,3-dioxa-cyclopropa[a]inden-6-yl ester 
• 109669-18-3 <2R-<2α,3β(S^*)>>-2-ethoxy-3,6-dihydro-3-(1'-thiophenyl-1'-carbomethoxy-3-nitropropyl)-2H-pyran 
• 109669-27-4 <4S-(4α,4aα,5β,7aα,7bα)>-5-ethoxy-3,4,4a,7,7a,7b-hexahydro-4-carbomethoxy-5-H-1,6-dioxa-2-azacyclopent(cd)indene 
• 109669-27-4 <4S-(4α,4aα,5α,7aα,7bα)>-5-ethoxy-3,4,4a,7,7a,7b-hexahydro-4-carbomethoxy-4-thiophenyl-5H-1,6-dioxa-2-azacyclopent(cd)indene 
• 109669-20-7 <4S-(3α,4aα,5α,7aα,7bα)>-5-ethoxy-3,4a,7,7a,7b-pentahydro-4β-<(t-butyldimethylsilyl)oxy>methyl-3,4-oxireno-1,6-dioxa-2-oxacyclopent(cd)indene 
• 109669-29-6 <4S-(4α,4aα,5α,7aα,7bα)>-5-ethoxy-4a,7,7a,7b-tetrahydro-4-<(t-butyldimethylsilyl)oxy>methyl-5H-1,6-dioxa-2-azacyclopent(cd)indene 
• 109669-22-9 <1R-(1α,6α,7aα)>-1-ethoxy-3,6,7a-trihydro-7β-<(t-butyldimethylsilyl)oxy>methyl-6,7-oxireno-cyclopenta(c)pyran-5-(1H)-one 
• 109669-21-8 <1R-(1α,4β,4aα,6α,7aα)>-1-ethoxy-3,4,4a,6,7a-pentahydro-4-hydroxy-7β-<(t-butyldimethylsilyl)-oxy>methyl-6,7-oxireno-cyclopenta(c)pyran-5-(1H)-one 

Relevant articles and documents

Total Synthesis of (+/-)-Specionin

(+/-)-Specionin has been synthesized in a short, efficient sequence of reactions from (+/-)-exo,exo-6,7-bis(benzyloxy)-exo-4-(hydroxymethyl)-cis-bicyclooct-2-ene 5.The key feature of the synthesis is a 'one-pot' hydrogenolysis-cyclopentadienol clea

Spruce budworm (Choristoneura fumiferana) antifeedants 4. Synthesis of specionin and biological studies

Specionin (1) was synthesized in seven steps from aucubin (2), an abundant iridoid form aucuba japonica. In a 'no-choice,' bioassay, specionin and several of its derivatives showed only modest antifeedant activity against the spruce budworm, while other derivatives were devoid of activity.

A GENERAL SYNTHETIC APPROACH TO OPTICALLY ACTIVE IRIDOID AGLYCONES. THE TOTAL SYNTHESES OF β-ETHYL DESCARBOMETHOXYVERBENALOL, ETHYL CATALPOL, AND (-)-SPECIONIN

A general approach to the synthesis of iridoid aglycones is reported.A combination Claisen rearrangement/nitrile oxide cycloaddition sequence has permitted the facile annulation of a highly functionalized cyclopentane ring onto a simple glycal derived fro

Total Synthesis of (-)-Specionin

The stereochemically discriminating, kinetic selection between the enantiotopically related alkene units in diene 3 was used to establish the absolute stereochemistry of the natural product specionin.Thus, reaction of 3 with glyoxylate 4R afforded the ene

IRIDOIDS : AN EFFICIENT CONVERSION OF (-)-CATALPOL INTO (-)-SPECIONIN

A partial synthesis of the antifeedant (-)-specionin (8) starting from the readily available (-)-catalpol (1) is described.It also allows the formation of analogs of 8 via specific transformations on intermediates 3 or 5 for screening of antifeedant prope

Total synthesis of specionin - natural product or artifact ?

The iridoid insect antifeedant specionin has been synthesised from endo-cis-bicyclo[3.3.0]oct-7-en-2-ol. When the bis acetal ring is cyclised at a late stage the correct stereochemistry is generated selectively.

IRIDOIDS: THE STRUCTURE ELUCIDATION OF SPECIONIN BASED ON CHEMICAL EVIDENCE AND 1H NMR ANALYSIS

The iridoid specionin is an effective antifeedant against the Eastern spruce budworm.Previous synthetic work has shown that the proposed structure was incorrect.Presently the total synthesis of the revised structure 2C is described.The structure elucidati