1354536-39-2

Upstream product

• 1354536-37-0 (1aS,2R,3aR,5S,7aR,7bS)-3a-cyano-1a,2,3,3a,4,5,7a,7b-octahydro-2,5-dimethylnaphtho[1,2-b]oxiren-7a-yl propionate 
• 1354536-38-1 (3S,3aS,4S,5aS,7R,8S,9bR)-2,3,3a,4,5,5a,6,7,8,9b-decahydro-8-hydroxy-3,4,7-trimethyl-2-oxonaphtho[1,2-b]furan-5a-carbonitrile 
• 93-97-0 benzoic acid anhydride 
• 335201-97-3 (3R,4aR,6S,8aS)-8a-Hydroxy-3,6-dimethyl-3,5,6,8a-tetrahydro-4H-naphthalene-4a-carbonitrile 
• 335202-06-7 Methanesulfonic acid (2R,3R,4aR,6S,7S,8aS)-4a-cyano-8a-hydroxy-7-methanesulfonyloxy-3,6-dimethyl-decahydro-naphthalen-2-yl ester 
• 335201-96-2 (2R,3R,4aR,6S,7S,8aS)-2,7,8a-Trihydroxy-3,6-dimethyl-octahydro-naphthalene-4a-carbonitrile 
• 335201-95-1 C₁₁H₁₃NO₃ 
• 335201-94-0 trans-8a-hydroxy-1,4,4a,5,8,8a-hexahydronaphthalene-4a-carbonitrile 
• 493-04-9 isotetraline 

Downstream Products

• 1354536-47-2 benzoic acid (3S,3aR,4S,5aS,7R,8S,9bR)-5a-cyano-3-hydroxy-3,4,7-trimethyl-2-oxo-2,3,3a,4,5,5a,6,7,8,9b-decahydronaphtho[1,2-b]furan-8-yl ester 
• 1354536-40-5 (3R,3aR,4S,5aS,7R,8S,9bR)-3-bromo-5a-cyano-2,3,3a,4,5,5a,6,7,8,9b-decahydro-3,4,7-trimethyl-2-oxonaphtho[1,2-b]furan-8-yl benzoate 
• 135645-83-9 11β-bromo-3,3-(ethylenedioxy)eudesmano-13,6α-lactone 

Relevant academic research and scientific papers

Towards the enantioselective synthesis of (-)-euonyminol-preparation of a fully functionalised lower-rim model

The development of a stereoselective total synthesis of β-dihydroagarofuran 4 is described. This compound contains the same oxygenation pattern on its 'lower-rim' as found in the natural sesquiterpene (-)-euonyminol (1) and it is expected that the route described should be applicable to the synthesis of that complex natural product. (-)-Euonyminol is found as the core scaffold of a series of complex macrodilactone sesquiterpenoids isolated from the Celastraceae which possess interesting biological activities (e.g. anti-HIV activity). The synthetic route builds upon an epoxidative asymmetric desymmetrisation of meso-diallylic alcohol 10 that we have reported previously. It features a lactate Ireland-Claisen rearrangement to establish the quaternary stereocentre at C11 (27 → 28a) and an unusual dealkylative intramolecular epoxide-opening by the C11 methyl ether to establish the tetrahydrofuranyl C-ring of the β-dihydroagarofuran skeleton (35 → 36). The Royal Society of Chemistry 2013.

An Ireland-claisen rearrangement/lactonisation cascade as a key step in studies towards the synthesis of (-)-euonyminol

Progress towards the asymmetric total synthesis of (-)-euonyminol is described with the focus on the installation of the -oxygenation pattern on the lower rim of the molecule. An Ireland-Claisen rearrangement/lactonisation cascade has been developed and studies towards further elaboration have uncovered an intriguing tunable diastereoselective -bromination of the resulting γ-lactone. Georg Thieme Verlag Stuttgart · New York.