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Usage

Uses

Used in Pharmaceutical Industry:
(1S,4aS)-methyl 6-methoxy-1,4a-dimethyl-9-oxo-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylate is used as a pharmaceutical intermediate for the synthesis of various medicinal compounds. Its unique structure and functional groups can be leveraged to create new drugs with specific therapeutic properties.
Used in Organic Synthesis:
In the field of organic synthesis, (1S,4aS)-methyl 6-methoxy-1,4a-dimethyl-9-oxo-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylate serves as a key building block for the creation of more complex organic molecules. Its phenanthrene core and functional groups can be utilized in the development of novel organic compounds with diverse applications.
Used in Other Industrial Applications:
Beyond pharmaceuticals and organic synthesis, (1S,4aS)-methyl 6-methoxy-1,4a-dimethyl-9-oxo-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylate may also find use in other industries. Its structural complexity and functional groups could be harnessed for specialized applications, such as in the development of new materials or chemical processes.

Upstream product

• 74-85-1 ethene 
• 1231-74-9 methyl 12-methoxypodocarpa-8,11,13-trien-19-oate 
• 4614-56-6 methyl podocarpate 
• 5947-49-9 podocarpic acid 
• 501-65-5 diphenyl acetylene 
• 623-43-8 methyl crotonate 
• 292638-85-8 acrylic acid methyl ester 
• 107-02-8 acrolein 
• 107-13-1 acrylonitrile 
• 78-94-4 methyl vinyl ketone 
• 1045-54-1 6α-Brom-7-oxo-O-methylpodocarpsaeure-methylester 
• 1231-74-9 methyl O-methylpodocarpate 

Downstream Products

• 1045-54-1 6α-Brom-7-oxo-O-methylpodocarpsaeure-methylester 
• 64597-67-7 (1S,2R,3S)-3-(2-Hydroxy-5-methoxy-phenyl)-2-methoxycarbonylmethyl-1,3-dimethyl-cyclohexanecarboxylic acid methyl ester 
• 23526-53-6 methyl 7β-hydroxy-12-methoxypodocarpa-8,11,13-trien-19-oate 
• 1865-97-0 methyl O-methyl-Δ^5,6-7-ketopodocarpate 
• 33169-07-2 (1S,4aS,10aR)-1,4a-Dimethyl-6-oxo-1,2,3,4,4a,6,7,8,10,10a-decahydro-phenanthrene-1-carboxylic acid 
• 23526-52-5 methyl 12-methoxypodocarpa-6,8,11,13-tetraen-19-oate 

Relevant academic research and scientific papers

Phenolic diterpenoid derivatives as anti-influenza a virus agents

A series of diterpenoid derivatives based on podocarpic acid were synthesized and evaluated as anti-influenza A virus agents. Several of the novel podocarpic acid derivatives exhibited nanomolar activities against an H1N1 influenza A virus (A/Puerto Rico/8/34) that was resistant to two anti-influenza drugs, oseltamivir and amantadine. This class of compounds inhibits the influenza virus by targeting the viral hemagglutinin-mediated membrane fusion. These results indicated that podocarpic acid derivatives may serve as potential drug candidates to fight drug-resistant influenza A virus infections.

Oxidations of 12-deoxy-, 12-hydroxy-, a 12-methoxy-, and 12-hydroxy-13-methoxypodocarpa-8,11,13-triene derivatives

Methods for the oxidation of the aryl ring of derivatives of podocarpic acid have been examined. Oxidation of methyl 12-hydroxypodocarpa-8,11,13-trien-19-oate (2) with phenyliodonium diacetate in various solvents gives 8β-substituted dienones. An 8β-chloro dienone is formed during oxidation of the phenol (2) with τ-butyl hypochlorite. Oxidation of (2) with dimethyldioxiran gives mainly the 7-ketone (13) but also affords the novel ε-lactone (26), while treatment with ruthenium tetraoxide also affords products of benzylic oxidation. Oxidation of methyl podocarpa-8,11,13-trien-19-oate (4) with m-chloroperbenzoic acid affords a B-ring lactone (29) and, unexpectedly, a 6αz-chloro 7-ketone (30). The action of cerium(IV) ammonium nitrate on (2) gives nitro derivatives rather than oxidation products. Oxidation of methyl 12-hydroxy-13-methoxypodocarpa-8,ll,13-trien-19-oate (22) with mchloroperbenzoic acid gives a low yield of a 7-oxo derivative (17) while treatment with ozone gives an unusual α,β-unsaturated γ-lactone (31), the hydroxy lactone (33), the unsaturated keto ester (34), and the substituted furan (35). Oxidation of (22) with Fremy's salt gives products of ring B oxidation. The structure of (31) has been confirmed by X-ray crystallography.

Skeletal rearrangements of ring C aromatic diterpenoids

The structure of a naphthalene derivative obtained by rearrangement of 13-methoxytotara-5,8,11,13-tetraen-7α-ol (2) has been revised to 5-(5′-isopropyl-6′-methoxy-2′-methyl-1′-naphthyl)-2- methylpent-2-ene (7). A minor oxidation product of 13-methoxytotar

Reaction with alkenes of η2-7-oxotetracarbonylmanganese complexes derived from diterpenoids

A number of activated 7-oxotetracarbonylmanganese(1) complexes derived from podocarpic acid (1) and from dehydroabietic acid have been coupled with alkenes to give C(14) functionalised derivatives in high yields.Some coupling reactions resulted in cyclization to C(7), forming 4H-acephenanthrylene derivatives in moderate yields.Several modes of activating these manganese complexes towards coupling reactions were investigated; these included oxidative decarbonylation at room temperature, thermal promotion, and palladium-mediation.

Coupling reactions of diterpenoid η2-tetracarbonylmanganese complexes with alkynes

A number of tetracarbonylmanganese complexes derived from podocarpic acid (1) have heen coupled with acetylene or diphenylacetylene to give steroidal analogues in high yield.Several modes of activating these manganese complexes towards coupling reactions

Reactions of η2-tetracarbonylmanganese complexes derived from podocarpic acid with electrophiles; functionalization of ring C

Reaction of tetracarbonylmanganese(I) complexes derived from podocarpic acid (1) with electrophilic bromine or iodine in CCl4 leads to 14-halogenated derivatives inaccessible by direct halogenation.Similar reactions in protic solvents lead to the formation of γ-lactones in high yield.The structure of one of these was established unequivocally by X-ray crystallograohy.Attempted oxidation of the C-Mn bond with a number of reagents proved generally to be unsuccessful.

Investigation of the antitumor activity of podocarpic acid derivatives

As a class, octahydrophenanthrene lactones, podolactones, and related podocarpic acid derivatives have been reported to possess a wide variety of biological activities, including antileukemic activity, inhibition of plant cell growth, and hormonal and anti-inflammatory properties. In the present study, a series of synthetic intermediates derived from podocarpic acid have been prepared and evaluated with the respect to their ability to inhibit human epidermoid carcinoma of the nasopharynx in vitro. The significant cytotoxicity demonstrated by methyl 6α-bromo-7-oxo-O-methylpodocarpate (50% inhibition at 8.85 x 10-9 M) was markedly higher than that of the other derivatives examined. Further evaluation against L210 and P388 lymphoid leukemias in mice failed to demonstrate significant antitumor activity.