ChemicalBook CAS DataBase List Brefeldin A

Brefeldin A synthesis

8synthesis methods

Product Name:Brefeldin A
CAS Number:20350-15-6
Molecular formula:C16H24O4
Molecular Weight:280.36

Brefeldin A, a commonly used protein transport inhibitor, specifically and reversibly blocks protein transport from the endoplasmic reticulum (ER) to the Golgi apparatus (Golgi). The fungus E. brefeldianum (ATCC 58665) was submerged and fermented at 25℃ with aeration and stirring to produce brefeldin A.

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Yield:-

Steps:

Multi-step reaction with 7 steps
1.1: DIAD; PPh₃ / tetrahydrofuran
2.1: Oxone; H₂O / methanol / 60 °C
3.1: potassium hexamethyldisilylazide / 1,2-dimethoxy-ethane / 1 h / -78 °C
3.2: 1,2-dimethoxy-ethane / -78 - 20 °C
4.1: CAN; H₂O / acetone
5.1: aq. NaOH / tetrahydrofuran; methanol
6.1: 61 percent / MsCl; Et₃N; 2,4,6-trichlorobenzoyl chloride / 4-DMAP / toluene / Heating
7.1: 77 percent / TBAF / tetrahydrofuran / 20 °C

References:

Trost, Barry M.;Crawley, Matthew L. [Journal of the American Chemical Society,2002,vol. 124,# 32,p. 9328 - 9329]