204375-31-5

Upstream product

• 67-56-1 methanol 
• 204375-30-4 (1R,5R,6R)-8-[1-Dimethylamino-meth-(E)-ylidene]-5-isopropyl-2-methyl-bicyclo[4.2.0]oct-2-en-7-one 
• 1026332-68-2 (1R,2R,6R)-2-(2,2-Dimethoxy-ethyl)-6-isopropyl-3-methyl-cyclohex-3-enecarboxylic acid methyl ester 
• 204375-28-0 (1R,5R,6R)-8,8-dichloro-5-isopropyl-2-methylbicyclo[4.2.0]oct-2-en-7-one 
• 204375-29-1 (1R,5R,6R)-5-Isopropyl-2-methyl-bicyclo[4.2.0]oct-2-en-7-one 

Downstream Products

• 204375-32-6 (1R,2R,6R)-2-[(S)-2-(5-Bromo-furan-2-yl)-2-hydroxy-ethyl]-6-isopropyl-3-methyl-cyclohex-3-enecarboxylic acid methyl ester 
• 234754-52-0 (3R,4aR,8R,8aR)-3-(5-Bromo-furan-2-yl)-8-isopropyl-5-methyl-3,4,4a,7,8,8a-hexahydro-isochromen-1-one 
• 204375-35-9 (2R,4R,5R,9R,11S)-11-(tert-Butyl-diphenyl-silanyloxy)-5-isopropyl-8-methyl-15-oxa-tricyclo[10.2.1.0^4,9]pentadeca-1⁽¹⁴⁾,7,12-trien-2-ol 
• 204375-23-5 {(1R,2R,6R)-2-[(S)-2-(5-Bromo-furan-2-yl)-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-6-isopropyl-3-methyl-cyclohex-3-enyl}-methanol 
• 204375-25-7 {(1R,2R,6R)-2-[(S)-2-(5-Bromo-furan-2-yl)-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-6-isopropyl-3-methyl-cyclohex-3-enyl}-acetonitrile 
• 204375-34-8 {(1R,2R,6R)-2-[(S)-2-(5-Bromo-furan-2-yl)-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-6-isopropyl-3-methyl-cyclohex-3-enyl}-acetaldehyde 
• 204375-33-7 (1R,2R,6R)-2-[(S)-2-(5-Bromo-furan-2-yl)-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-6-isopropyl-3-methyl-cyclohex-3-enecarboxylic acid methyl ester 
• 204375-36-0 2,2-Dimethyl-propionic acid (2R,4R,5R,9R,11S)-11-(tert-butyl-diphenyl-silanyloxy)-5-isopropyl-8-methyl-15-oxa-tricyclo[10.2.1.0^4,9]pentadeca-1⁽¹⁴⁾,7,12-trien-2-yl ester 
• 204375-24-6 Methanesulfonic acid (1R,2R,6R)-2-[(S)-2-(5-bromo-furan-2-yl)-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-6-isopropyl-3-methyl-cyclohex-3-enylmethyl ester 
• 174545-76-7 eleutherobin 

Relevant academic research and scientific papers

The total synthesis of eleutherobin

The total synthesis of the title compound (1), starting with (R)-( - )-α-phellandrene (6), has been accomplished. The synthesis rigorously proves the relative stereochemical relationship of the diterpenoid and carbohydrate domains of eleutherobin. Key reactions included a Nozaki - Kishi ring closure to produce a furanophane (see 37 → 38), a pyranose to furanose transposition (see 50 → 47), and a novel oxycarbaglycosidation (cf. 58 → 87) for joining the two domains.

A convergent route for the total synthesis of the eleuthesides

A ring expansion/ring contraction sequence is one of the key steps in the stereoselective synthesis of the tricyclic eleutheside skeleton 2 from α-phellandrene 1. Eleuthesides are natural products that are isolated from different marine sources, and sever