172919-07-2

Upstream product

• 1122-91-4 4-bromo-benzaldehyde 
• 105515-33-1 (2E)-3-(4-bromophenyl)prop-2-en-1-ol 
• 3282-30-2 pivaloyl chloride 
• 24393-53-1 ethyl (E)-3-(4-bromophenyl)-2-propenoate 

Downstream Products

• 172919-12-9 C₂₅H₂₂O₅ 
• 117709-78-1 combretastatin D-1 
• 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 
• 202645-49-6 combretastatin D-1 benzyl ether 
• 202645-48-5 combretastatin D-2 benzyl ether 
• 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 
• 172919-05-0 (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 
• 126191-23-9 combretastatin D-2 
• 172919-08-3 2,2-Dimethyl-propionic acid (E)-3-{4-[2-benzyloxy-5-(2-ethoxycarbonyl-ethyl)-phenoxy]-phenyl}-allyl ester 

Relevant academic research and scientific papers

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

Total synthesis of natural (-)combretastatin D-1

Combretastatin D-1, (2), was synthesized via a 12 step sequence. Sharpless asymmetric dihydroxylation was used in order to introduce the appropriate asymmetry. Regiospecific cyclodehydration of the diol 3 gave the title compound in 96% ee.