53823-04-4

Usage

Uses

Used in Sports Medicine and Bodybuilding:
4,4,8-Trimethyl-16-oxa-18-nor-5α-androsta-12-ene-17-one is used as an anabolic agent for its ability to enhance athletic performance and increase muscle mass. Its potent effects on muscle growth make it a sought-after substance among athletes and bodybuilders seeking to improve their physical capabilities.
However, it is important to note that the use of 4,4,8-Trimethyl-16-oxa-18-nor-5α-androsta-12-ene-17-one is restricted in many countries due to its potential for abuse and the adverse health effects that may arise from its use. The misuse of 4,4,8-Trimethyl-16-oxa-18-nor-5α-androsta-12-ene-17-one can lead to serious health risks, and it is crucial to adhere to the regulations and guidelines set forth by relevant authorities to ensure safe and responsible use.

Upstream product

• 14022-44-7 podocarp-8⁽¹⁴⁾-en-13-one 
• 79981-26-3 (3aS,3bR,5aS,9aS,9bR)-3b,6,6,9a-Tetramethyl-3a,3b,4,5,5a,6,7,8,9,9a,9b,10-dodecahydro-1H-phenanthro[1,2-c]furan-3-one 
• 59909-44-3 (10S,14R)-(-)-isoagath-12-en-15-ol 
• 79926-27-5 methyl 12α-hydroxy-isoanticopal-13(16)-en-15-oate 
• 59909-34-1 methyl (14R)-isogath-12-en-15-oate 
• 183254-53-7 14α-Hydroxymethyl-8β-methylpodocarpan-13-one 
• 183254-54-8 (1R,4aS,4bR,8aR,10aS)-1,2,3,4,4a,4b,5,6,7,8,8a,9,10,10a-tetradecahydro-4b,8,8,10a-tetra-methyl-2-oxo-trans-anti-trans-phenanthene-1-methanol 
• 183137-48-6 8-β-Methylpodocarp-13-en-13-yl trifluoroacetate 
• 183137-47-5 15,16-Dinorlabd-13-yn-8β-ol 
• 71876-56-7 (+)-8α,14-epoxypodocarpan-13-one 
• 71876-55-6 (-)-15,16,17-trinorlabd-13-yn-8-one 
• 201230-82-2 carbon monoxide 
• 53771-93-0 (14R)-isoagath-12-ene-15,16-diol 
• 79191-22-3 (1R,3R,4aS,4bR,8aR,10aS)-3-Hydroxy-4b,8,8,10a-tetramethyl-2-methylene-tetradecahydro-phenanthrene-1-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Podocarpane-to-spongian skeleton conversion. Synthesis of (+)-isoagatholactone and (-)-spongia-13(16),14-diene

A stereoselective synthesis of the spongian diterpenes (+)-isoagatholactone 5 and (-)-spongia-13(16),14-diene 6 is achieved starting from (+)-podocarp-8(14)-en-13-one 3 (R=H) via the common intermediate β-hydroxy ketone 13.

CYCLIZATION AND REARRANGEMENT OF DITERPENOIDS. SYNTHESIS OF ISOAGATHOLACTONE AND METHYL SPONGIA-13(16),14-DIEN-19-OATE

The synthesis of isoagatholactone has been effected by the successive oxidation of (14)R-isoagath-12-en-15-ol with selenium dioxide and manganese dioxide.Methyl spongia-13(16),14-dien-19-oate has been obtained by the cyclization of methyl lambertianate with 100percent sulfuric or fluorosulfonic acid.

Stereoselective Total Syntheses of (+/-)-Isoagatholactone and (+/-)-12α-Hydroxyspongia-13(16),14-diene, Two Marine Sponge Metabolites

The highly efficient, stereoselective syntheses of (+/-)-isoagatholactone (1a) and (+/-)-12α-hydroxyspongia-13(16),14-diene (3e), a fundamental skeleton of spongiadiol (3a) and its related furanoid diterpenes, are described. (+/-)-Labda-8(20),13-dien-15-oic acid (6), chosen as the starting material, was cyclised to the known tricyclic compound (2b), which after methylation was subjected to photooxygenation, yielding the allylic alcohol (7a).Refluxing of the alcohol (7a) with 3.5percent sulphuric acid in dioxan afforded the lactone (1b), which after reduction with lithium aluminium hydride led to the diol (2g).Subsequent oxidation of this diol with Collins reagent provided the desired compound (1a).The key precursor for the synthesis of compound (3e) was the allylic alcohol (7a) obtained above.On epoxidation the alcohol (7a) gave the epoxide (13), which by the action with lithium di-isopropylamide led to the α,β-unsaturated γ-lactone (14).Subsequent reduction of this lactone with di-isobutylaluminium hydride afforded the furan (3e).

TOTAL SYNTHESES OF (+/-)-ISOAGATHOLACTONE AND (+/-)-12α-HYDROXYSPONGIA-13(16),14-DIEN

(+/-)-Isoagatholactone 1 and (+/-)-12α-hydroxyspongia-13(16),14-dien 2b, a fundamental skeleton of spongiadiol 2a and its congeners, have been synthesized from (+/-)-labda-8(20),13-dien-15-oic acid 3.

Stereoselective Synthesis of the Novel Marine Diterpene (+)-Isoagatholactone

The synthesis of (+)-isoagatholactone (1) from (+)-manool (4) via the key intermediate ent-methyl isocopalate (2) is described.