77012-32-9

Upstream product

• 38011-83-5 trans-1-(4,8-dimethylnona-3,7-dien-1-yl)-4-methoxybenzene 
• 37715-31-4 (E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-enyl acetate 
• 38769-92-5 4-methoxybenzylmagnesium chloride 
• 31179-52-9 p-anisylmagnesium bromide 
• 35162-74-4 geranyl phenyl sulfide 
• 20401-88-1 3-(4-methoxyphenyl)propional 
• 4586-91-8 1-methoxy-4-(4-methylpent-3-en-1-yl)benzene 
• 709667-29-8 C₁₈H₂₇BrO₂ 
• 5389-87-7 1-chloro-3,7-dimethylocta-2,6-diene 
• 824-94-2 p-methoxybenzyl chloride 

Downstream Products

• 77012-36-3 cis-3-(2-p-Methoxyphenylethyl)-2,3,4-trimethylcyclohexanone 
• 77012-35-2 cis-3-(2-p-Methoxyphenylethyl)-2,2,4-trimethylcyclohexanone 
• 77012-41-0 2-((3aS,9bS)-8-Methoxy-9b-methyl-2,3,3a,4,5,9b-hexahydro-1H-cyclopenta[a]naphthalen-3-yl)-propan-2-ol 
• 10064-10-5 6-methoxy-1,1,4a-trimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-2-ol 
• 83999-80-8 (E)-9-(4-Methoxy-phenyl)-2,6-dimethyl-nona-1,6-dien-3-ol 
• 83999-79-5 ((1S,2S,4aR,10aS)-2-Benzyloxy-6-methoxy-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-1-yl)-methanol 

Relevant academic research and scientific papers

The synthesis and antibacterial activity of pyrazole-fused tricyclic diterpene derivatives

The diterpenoid compound 5 was identified as an antibacterial lead in our screening of small synthetic natural product-like (NPL) library. A series of novel diterpene derivatives were synthesized and investigated for their activity against Staphylococcus

Discovery of methylpyrimidine ring-fused diterpenoid analogs as a novel testosterone synthesis promoter

Herein we screened our small synthetic library of diterpenoid analogs for hit compounds on promoting testosterone synthesis and the methylpyrimidine ring-fused diterpenoid analog 7 was obtained as the hit. Based on the hit, a series of derivatives were de

A Relay Strategy Actuates Pre-Existing Trisubstituted Olefins in Monoterpenoids for Cross-Metathesis with Trisubstituted Alkenes

A retrosynthetic disconnection-reconnection analysis of epoxypolyenes - substrates that can undergo cyclization to podocarpane-type tricycles - reveals relay-actuated Δ6,7-functionalized monoterpenoid alcohols for ruthenium benzylidene catalyzed olefin cross-metathesis with homoprenyl benzenes. Successful implementation of this approach provided several epoxypolyenes as expected (E/Z, ca. 2-3:1). The method is further generalized for the cross-metathesis of pre-existing trisubstituted olefins in other relay-actuated Δ6,7-functionalized monoterpenoid alcohols with various other trisubstituted alkenes to form new trisubstituted olefins. Epoxypolyene cyclization of an enantiomerically pure, but geometrically impure, epoxypolyene substrate provides an enantiomerically pure, trans-fused, podocarpane-type tricycle (from the E-geometrical isomer).

Indium tribromide-promoted arene-terminated epoxy olefin cyclization

An arene-terminated epoxy olefin cyclization was promoted by a water-tolerant Lewis acid to give tri- and tetracyclic 3β-hydroxy terpenoids and steroid derivatives in 57 and 37% yields, respectively, per new formed ring up to 75%. The Royal Society of Chemistry.

Transition-metal-catalyzed allylic substitution and titanocene-catalyzed epoxypolyene cyclization as a powerful tool for the preparation of terpenoids

Many biologically active substances are composed of sesquiterpene units linked to aromatic structures, especially substituted phenols. Here, we describe an efficient synthetic approach to this class of natural product from commercially available substances in a short sequence. The key transformations involve allylic substitution reactions using a palladium or copper catalyst and titanocene-catalyzed epoxypolyene cyclization reactions via radicals. The polycyclic core structures are accessed with high chemo- and stereocontrol. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Efficient and stereoselective synthesis of precursors for epoxypolyene cyclizations via allylic substitutions

A catalytic and highly stereoselective approach to precursors for epoxypolyene cyclizations based on copper-catalyzed allylic substitutions is described. The method allows introduction of various aromatic, benzyl, and alkyl groups without affecting epoxides. The compounds obtained are valuable starting materials for the synthesis of natural products and biologically active substances. Georg Thieme Verlag Stuttgart.

Cyclisation Reactions: Part VI - Further Study in Biogenetic-type Cyclisation of Epoxy-Olefins

(6E)-9-p-Methoxyphenyl-2,6-dimethylnona-2,6-diene (I) on mono-epoxidation affords mainly 2,3-epoxyolefin (IV) admixed with some 6,7-isomer.IV on cyclisation with boron trifluoride etherate furnishes three ketones: 7-oxo-9-p-methoxyphenyl-2,6-dimethylnon-2-ene (XIII) presumably formed from 6,7-epoxyolefin (XII), cis-3-(2-p-methoxyphenylethyl)-2,2,4-trimethylcyclohexanone (XIV) arising out of 1,4-hydride transfer in an intermediate cyclohexyl cation (XVII), and cis-3-(2-p-methoxyphenylethyl)-2,3,4-trimethylcyclohexanone (XV) resulting from three consecutive 1,2-H, Me shifts in the same intermediate.In addition, 12-methoxypodocarpa-8,11,13-trien-3β-ol (IX) is obtained in 10 percent yield.The mono-epoxide (V) from the corresponding 3-isopropyl-4-methoxyphenyldiene (II) on similar cyclisation affords, among others, hinokiol methyl ether (X) and another crystalline compound characterised by PMR and MS as 12-methoxy-13-isopropyl-A-homo-4a-oxapodocarpa-8,11,13-trien-3β-ol (XXII).The latter is formed by a concerted cyclisation of the di-epoxide (XXI) present in the starting material.Contrary to a previous report from this laboratory, it is now found that trans-podocarpa-8,11,13-trienes (XXV) are more stable than the cis-isomers and are almost the sole products of cyclisation of 2-(2-arylethyl)-1,3,3-trimethylcyclohexyl cations (XXIV) and their analogues under thermodynamically controlled condition.