61038-90-2

Basic information

• Product Name: (-)-isostegane
• CAS NO: 61038-90-2
• Molecular Weight: 398.412
• Mol File: 61038-90-2.mol
• Article Data: 15

Chemical Properties

• CAS DataBase Reference: (-)-isostegane(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-isostegane(61038-90-2)
• EPA Substance Registry System: (-)-isostegane(61038-90-2)

Safety Data

• Hazardous Substances Data: 61038-90-2(Hazardous Substances Data)

Upstream product

• 92232-57-0 (3S,4S,5S)-3-Benzo[1,3]dioxol-5-ylmethyl-4-(3,4,5-trimethoxy-benzyl)-5-trityloxymethyl-dihydro-furan-2-one 
• 61441-09-6 methyl 6-bromo-1,3-benzodioxole-5-carboxylate 
• 69998-63-6 (+/-)-epipicrosteganol-8 
• 69998-63-6 (+/-)-8α-hydroxyisopicrostegane 
• 17301-91-6 (3R*,4R*)-3-(3,4,5-trimethoxybenzyl)-4-(3,4-methylenedioxybenzyl)-4,5-dihydro-2(3H)-furanone 
• 120-57-0 piperonal 
• 61038-90-2 (-)-isostegane 
• 40456-50-6 yatein 
• 76236-33-4 (3S,4S)-(+)-3-(2-(3,4,5-trimethoxyphenyl)-1,3-dithiane-2-yl)-4-trityloxymethyl-butan-4-olide 
• 76236-34-5 (4S,5S)-4-(3,4,5-Trimethoxy-benzyl)-5-trityloxymethyl-dihydro-furan-2-one 
• 76236-36-7 (2S,3S,4S)-(+)-3-(3',4',5'-trimethoxybenzyl)-4-piperonyl-1,2,5-pentanetriol 
• 72627-54-4 (3S,4S)-(+)-2-hydroxy-3-(3',4',5'-trimethoxybenzyl)-4-piperonyl-tetrahydrofurane 
• 76236-35-6 (3S,4S)-(+)-3-(3,4,5-trimethoxybenzyl)-4-hydroxymethyl-butan-4-olide 
• 72627-52-2 (2S,3S,4S)-(+)-2-piperonyl-3-(3,4,5-trimethoxybenzyl)-4-hydroxymethyl-butan-4-olide 

Downstream Products

• 61038-90-2 (+/-)-picrostegane 
• 41451-71-2 (+/-)-steganol 
• 92232-58-1 (+/-)-4-bromostegane 
• 61038-90-2 (-)-isopicrostegane 
• 61038-90-2 trans-6-(hydroxymethyl)-10,11,12-trimethoxy-2,3-methylenedioxy-dibenzo[1a,4a:8a,12a]cyclooctadiene-7-carboxylic acid lactone 
• 61038-90-2 (-)-picrostegane 
• 61038-90-2 (+)-stegane 
• 41451-68-7 (+/-)-steganacin 
• 41451-68-7 (+/-)-episteganacin 
• 41451-68-7 (+)-episteganacin 
• 41451-68-7 (+)-steganacin 
• 41451-68-7 (+)-steganacin 
• 96960-68-8 (1S^*,2S^*,7aR^*,7bR^*)-1-pyrrolidinocarbonyl-2-benzoyloxymethyl-5,6-methylenedioxy-8,9,10-trimethoxy-1,2,3,12-tetrahydrobenzo<4.5:6.7>cyclooctene 
• 41451-71-2 (-)-steganol 

Relevant articles and documents

A practical method for the oxidative coupling of aromatic compounds

A practical method for the oxidative coupling reaction of phenolic and nonphenolic compounds is described. The versatility of this reaction was demonstrated by the successful coupling of the wide variety of substrates including catecholic compounds and known intermediates for the synthesis of steganacin and its analogs.

Oxidative cyclisation of cis- and trans-2,3-dibenzylbutyrolactones using ruthenium tetra(trifluoroacetate)

A series of cis- and trans-2,3-dibenzylbutyrolactones have been synthesised and subjected to oxidative cyclisation using ruthenium tetra(trifluoroacetate) affording dibenzocyclooctadiene lactones belonging to the stegane and isostegane series of lignans.

TRIP-Catalyzed Asymmetric Synthesis of (+)-Yatein, (-)-α-Conidendrin, (+)-Isostegane, and (+)-Neoisostegane

The asymmetric allylation under the assistance of catalytic amounts of 3,3′-bis(2,4,6-triisopropylphenyl)-1,1′-binaphthyl-2,2′-diyl hydrogen phosphate (TRIP) allows the concise construction of the lignan scaffold from simple aldehydes and allylic bromides with full control of the two formed stereocenters. This young methodology has been employed to synthesize four naturally and pharmaceutically active lignans. Members of the dibenzylbutyrolactone, the tetraline, and the dibenzocyclooctadiene classes have been synthesized in 40-47% overall yield along four-step synthetic routes.

A general approach to the asymmetric synthesis of lignans: (-)-methyl piperitol, (-)-sesamin, (-)-aschantin, (+)-yatein, (+)-dihydroclusin, (+)-burseran, and (-)-isostegane

A highly efficient, diastereo- and enantioselective route was developed to access a great variety of lignans. The asymmetric synthesis of the 2,3-disubstituted γ-butyrolactones 9a-c could be improved in the case of aldol reactions by employing 2.2 equivalents of LiCl as an additive to provide, after purification, highly diastereo- and enantioenriched starting materials for the synthesis of the furofuran lignans (-)-methyl piperitol, (-)-sesamin, and (-)-aschantin. Furthermore, the γ-butyrolactone 15 was converted into dibenzylbutyrolactone lignan (+)-yatein, the dibenzylbutandiol type (+)-dihydroclusin, the tetrahydrofuran type (+)-burseran, and the dibenzocyclooctadiene type (-)-isostegane.