202645-48-5

Upstream product

• 1146133-44-9 3'-(4'''-bromophenyl)-2'Z-propenyl 3-(3''-hydroxy-4''-benzyloxyphenyl)propanoate 
• 172919-13-0 2,2-Dimethyl-propionic acid (2R,3R)-3-{4-[2-benzyloxy-5-(2-carboxy-ethyl)-phenoxy]-phenyl}-2,3-bis-(tert-butyl-dimethyl-silanyloxy)-propyl ester 
• 172919-15-2 ethyl 3-(3'-hydroxy-4'-benzyloxyphenyl)-2E-propenoate 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 100-39-0 benzyl bromide 
• 105515-33-1 (2E)-3-(4-bromophenyl)prop-2-en-1-ol 
• 24393-53-1 ethyl (E)-3-(4-bromophenyl)-2-propenoate 
• 4049-39-2 4-benzyloxy-3-hydroxy-benzaldehyde 
• 172919-05-0 (13R,14R)-4-benzyloxy-13,14-dihydroxy-2,11-dioxatricyclo[13.2.2.1^3,7]eicosa-1⁽¹⁸⁾,3,5,7⁽²⁰⁾,1⁽¹⁹⁾,16-hexaen-10-one 
• 172919-09-4 2,2-Dimethyl-propionic acid (2R,3R)-3-{4-[2-benzyloxy-5-(2-ethoxycarbonyl-ethyl)-phenoxy]-phenyl}-2,3-bis-(tert-butyl-dimethyl-silanyloxy)-propyl ester 
• 202645-46-3 3-(4-Benzyloxy-3-{4-[(1R,2R)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-propyl]-phenoxy}-phenyl)-propionic acid 
• 172919-11-8 (13R,14R)-4-Benzyloxy-13,14-bis-(tert-butyl-dimethyl-silanyloxy)-2,11-dioxa-tricyclo[13.2.2.1^3,7]icosa-1⁽¹⁸⁾,3,5,7⁽²⁰⁾,15⁽¹⁹⁾,16-hexaen-10-one 
• 172919-06-1 2,2-Dimethyl-propionic acid (2R,3R)-3-{4-[2-benzyloxy-5-(2-ethoxycarbonyl-ethyl)-phenoxy]-phenyl}-2,3-dihydroxy-propyl ester 
• 172919-08-3 2,2-Dimethyl-propionic acid (E)-3-{4-[2-benzyloxy-5-(2-ethoxycarbonyl-ethyl)-phenoxy]-phenyl}-allyl ester 

Downstream Products

• 126191-23-9 combretastatin D-2 

Relevant academic research and scientific papers

Antineoplastic agents. 565. Synthesis of combretastatin D-2 phosphate and dihydro-combretastatin D-2

A modified synthetic route to combretastatin D-2 (5) was devised in order to further evaluate its biological activity, for its conversion to phosphate prodrugs (25-28), and as a route to obtaining dihydro-combretastatin D-2 (42). A parallel first total synthesis of dihydro-combretastatin D-2 was completed, proceeding from a saturated 3-phenylpropionic ester intermediate via the Ullmann biaryl ether reaction (39-41). In contrast to the cancer cell growth inhibitory activity exhibited by combretastatin D-2, relatively minor structural modifications (41, 42) caused elimination of those properties.

Total synthesis of combretastatins D

The 15-membered caffrane ring of the natural product group of combretastatins D is synthesized in high yield with suitably functionalized saturated seco acids. The key step is a Mitsunobu-type macrolactonization. A common synthon is used for the construct