16826-83-8

Usage

Uses

Used in Pharmaceutical Industry:
(1S)-1,4aβ-Dimethyl-6-methoxy-1,2,3,4,4a,9,10,10aα-octahydrophenanthrene-1β-carbaldehyde is used as a building block for the synthesis of various pharmaceuticals due to its unique structural properties and aromatic aldehyde functional group, which can be utilized in the development of new drugs and therapeutic agents.
Used in Fragrance Industry:
(1S)-1,4aβ-Dimethyl-6-methoxy-1,2,3,4,4a,9,10,10aα-octahydrophenanthrene-1β-carbaldehyde is used as a precursor in the production of fragrances, taking advantage of its aromatic properties to create unique scents and enhance the sensory experience of various products.
Used in Organic Chemistry Research:
(1S)-1,4aβ-Dimethyl-6-methoxy-1,2,3,4,4a,9,10,10aα-octahydrophenanthrene-1β-carbaldehyde is used as a research compound in organic chemistry, where its complex structure and functional groups can be studied and manipulated to gain insights into chemical reactions and mechanisms.
Used in Novel Materials Development:
(1S)-1,4aβ-Dimethyl-6-methoxy-1,2,3,4,4a,9,10,10aα-octahydrophenanthrene-1β-carbaldehyde is used as a component in the development of novel materials, leveraging its unique structural properties to create innovative materials with potential applications in various industries.

InChI:InChI=1/C18H24O2/c1-17(12-19)9-4-10-18(2)15-11-14(20-3)7-5-13(15)6-8-16(17)18/h5,7,11-12,16H,4,6,8-10H2,1-3H3

Upstream product

• 16826-86-1 12-O-methylpodocarpol 
• 10037-26-0 O-methylpodocarpic acid 
• 10064-08-1 (+)-(5S,10S)-12-methoxypodocarpa-8,11,13-triene 
• 74-88-4 methyl iodide 
• 63478-76-2 1-hydroxy-6-heptyne 
• 637-69-4 4-Methoxystyrene 
• 4831-48-5 6-Methoxy-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1-carbaldehyde 
• 154903-59-0 (1R,4aS,10aR)-6-Methoxy-1,4a-dimethyl-2-oxo-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 154903-60-3 (-)-Phenylmenthyl (+)-O-methylpodocarpate 
• 192199-24-9 (1R,3R,4S)-8-phenylmenthyl 2-methylacetoacetate 
• 154807-78-0 Ethyl 2-methyl-5-(4-methoxyphenyl)-2(E)-pentenoate 
• 154807-80-4 5-(4-Methoxyphenyl)-2-methyl-2(E)-penten-1-ol 
• 154807-81-5 1-Bromo-5-(4-methoxyphenyl)-2-methyl-2-pentene 
• 5406-18-8 3-(p-methoxyphenyl)-1-propanol 

Downstream Products

• 10037-26-0 O-methylpodocarpic acid 
• 16826-86-1 12-O-methylpodocarpol 
• 115376-07-3 12-O-methylpodocarpal oxime 

Relevant academic research and scientific papers

Photoinduced Skeletal Rearrangements Reveal Radical-Mediated Synthesis of Terpenoids

Herein, we describe the protecting-group-free total synthesis of two structurally diverse Isodon diterpenoids, (+)-ent-kauradienone (3) and (?)-jungermannenone C (4), in 12 and 14 steps respectively, through sequential applications of three radical-based

Syntheses of Skeletally Diverse Tetracyclic Isodon Diterpenoid Scaffolds Guided by Dienyne Radical Cyclization Logic

We report herein the diversity-oriented synthesis of various tetracyclic Isodon diterpenoid scaffolds guided by radical cyclization logic. Our substrate-based dienyne radical cyclization approach is distinctive from reagent-based rearrangement approaches

Concise total syntheses of palominol, dolabellatrienone, β-araneosene, and isoedunol via an enantioselective Diels-Alder macrobicyclization

Concise total syntheses of four members of the dolabellane family of diterpenoid natural products are reported. Key features of the developed route include the first demonstration of an enantioselective, intramolecular Type I Diels-Alder macrobicyclization, the first example of a stereoselective π-allyl Stille coupling reaction involving a farnesyl-derived intermediate, a powerful new reagent for the formation of dithianes with acid-sensitive molecules, and a unique and highly efficient ring-contraction sequence based on a modified Wolff photochemical rearrangement. Copyright

Synthesis of trinorditerpenoid derivatives and evaluation of antimicrobial and cytotoxic activity

The synthesis of optically active trinorditerpenes was carried out, and their antimicrobial and antitumor activity was tested. The synthetic derivative 12-hydroxypodocarpa-8,11,13-triene (7) showed GI50 at 6.6 μM against breast cancer MDA-MB-43

Structure - Activity relationship of Aza-steroids as PI-PLC inhibitors

A number of aza-steroids were synthesized as potent phosphatidylinositol phospholipase C (PI-PLC) inhibitors. The epimeric mixtures 22,25-diazacholesterol (8a) and 3β-hydroxy-22,25-diazacholestane (8b) were among the most active of these inhibitors, with IC50 values of 7.4 and 7.5 μM, respectively. The 20α epimer, 8a2 (IC50 = 0.64 μM), whose stereochemistry at C-20 coincides with that of cholesterol, was found 50 times more potent than the 20β epimer, 8a1 (IC50 = 32.2 μM). In diaza-estrone derivatives, the 3-methoxy group on the aromatic A-ring of 23 exhibited moderate PI-PLC inhibitory activity (IC50 = 19.7 μM), while compound with a free hydroxyl group (21) was inactive. However, in diaza-pregnane derivatives, epimers with a 3-hydroxyl group (8a, IC50 = 7.4 μM) exhibited more potent PI-PLC inhibitory activity than their counterparts with 3-methoxyl group on the non-aromatic A-ring (26, IC50 = 17.4 μM). We have illustrated in our previous publication that 3-hydroxyl-6-aza steroids are potent PI-PLC inhibitors. However, simultaneous presence of the 6-aza and 22,25-diaza moieties in one molecule as in 13, led to loss of activity. Epimeric mixture 8a showed selective growth inhibition effects in the NCI in vitro tumor cell screen with a mean GI50 value (MG-MID) of 5.75 μM for 54 tumors.

A general asymmetric access to the podocarpane diterpenoids

An efficient and enantiocontrolled total synthesis of (+)-O-methylpodocarpic acid 2 has been accomplished by employing a combined strategy of the lipase-mediated kinetic resolution of the tricyclic allyl alcohol (±)-7 and a highly diastereoselective silylmethyl radical cyclization of 5 leading to the tetracyclic silyl ether 4.

Asymmetric Induction in Mn(III)-Based Oxidative Free-Radical Cyclizations of Phenylmenthyl Acetoacetates and 2,5-Dimethylpyrrolidine Acetoacetamides

Mn(III)-based oxidative free-radical cyclization of phenylmenthyl ester 1e afforded 90percent of 13 with 86percent de.Cyclization of 31b provided 56percent of (+)-podocarpic acid precursor 32e with 82percent de.The direction of de was opposite in these two cases.Oxidative cyclization of α-methyl β-keto ester 44b gave a 1:1.6 mixture of 46b and 47b while α-propyl β-keto ester 44d produced a >10:1 mixture of 46d and 47d indicating that the extent and direction of de is dependent on the size of the α-substituent.The reaction proceeds through transition states 12 and 56 with large α-substituents and through transition states 19 and 57 with small α-substituents.The de depends on the double-bond substitution pattern as shown by the decreased de with 37b and 37d, and selectivity in the 5-exo cyclization of 64b, 65b, 70b, and 71b is low.

Synthesis of Winterin from Podocarpic Acid

Ozonolysis of a hydroquinone derived from podocarpic acid (1) gave the biologically active natural product winterin (11).Treatment of the quinone (12) with ozone bave a ring-contracted spiro furanone, the mechanism of formation of which is proposed.

Chemistry of the Podocarpaceae. LX The preparation of Homologues of Ambrox and Isoambrox from Podocarpic Acid

Derivatives of podocarpic acid (5) have been converted into the homologues (22) (23) (24) (26) (27) and (28) of the cyclic ethers Ambrox (25) and Isoambrox (29).All possess ambergris-like odours.