151409-32-4

Upstream product

• 106-28-5 Farnesol 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 151409-23-3 tert-butyldiphenyl {[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]oxy}silane 

Downstream Products

• 171420-01-2 (2E,6E)-<10-3H>-1-((tert-butyldiphenylsilyl)oxy)-3,7,11-trimethyl-2,6,10-dodecatriene 
• 171420-00-1 (2E,6E)-<10-3H>-1-((tert-butyldiphenylsilyl)oxy)-3,7-dimethyl-2,6-decadien-10-al 
• 171419-99-1 (2E,6E)-<10-3H>-1-((tert-butyldiphenylsilyl)oxy)-3,7-dimethyl-2,6-decadien-10-ol 
• 171419-97-9 (2E,6E)-1-((tert-butyldiphenylsilyl)oxy)-3,7-dimethyl-2,6-decadien-10-al 
• 151409-24-4 tert-butyl(((2E,6E)-9-(3,3-dimethyloxiran-2-yl)-3,7-dimethylnona-2,6-dien-1-yl)oxy)diphenylsilane 

Relevant academic research and scientific papers

Total syntheses of parthenolide and its analogues with macrocyclic stereocontrol

The first total synthesis of parthenolide (1) is described. The key feature of this synthesis is the formation of a 10-membered carbocylic ring by a macrocyclic stereocontrolled Barbier reaction, followed by a photoinduced Z/E isomerization. The biological evaluation of a small library of parthenolide analogues (19, 33, and 34) disclosed a preliminary structure-activity relationship (SAR). The results revealed that the C1, C10 double bond configuration of parthenolide has little or no effect on the activity, and the C6 and C7 configurations of the lactone ring have a moderate impact on the activities against some cancer cell lines.

Synthesis of (2E,6E)-[10-3H]farnesol and (2E,6E)-[10-3H]farnesal for insect dehydrogenase studies

[10-3H]Farnesol ((2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-ol) and [10-3H]farnesal ((2E,6E)-3,7,11-trimethyl-2,6,10- -dodecatrian-1-al) were synthesized by sequential reduction and oxidation of the corresponding tert-butyldiphenylsilyl protected 11,12,13-trisnoraldehyde, followed by Wittig homologation using isopropyltriphenylphosphorane. Direct reduction of the C-12 allylic bromide or allylic chloride proved to be an nonviable method, resulting in either multiple decomposition products or significant double bond transposition. Oxidation of the [10-3H]labelled trisnoralcohol with pyridinium chlorochromate resulted in essentially complete retention of the radiolabel as was established for the corresponding deuterated material. [3H]labelled farnesol and farnesal were obtained in 78% and 74% yields, respectively, from the trisnoraldehyde. These materials were used as radiotracers for examining the enzymatic activity of insect farnesol and farnesal dehydrogenase, key enzymes in the biosynthesis of juvenile hormone.