Granted Patent B2

US 12,698,264 · App. 18/264,939 · Granted Aug 4, 2026

Inventors: Paul A. Wender (Menlo Park, CA); Nguyen Hong Quang Luu (Menlo Park, CA); Zachary Gentry (Palo Alto, CA); Edward Njoo (Freemont, CA); David Fanelli (Stanford, CA); Owen Dennis McAteer (Stanford, CA)

Assignee: THE BOARD OF TRUSTEES OF THE LELAND STANFORD JUNIOR UNIVERSITY

C07D303/14A61K31/122A61K36/47A61K2236/15A61K2236/33A61K2236/53

Abstract

Claims (12)

1 . A method for the synthesis of tigilanol tiglate, precursors, and analogs thereof, the method comprising the steps as shown in the schema shown in FIG. 3 of the disclosure.

2 . A method for the synthesis of tigilanol tiglate, the method comprising the steps as shown in the schema shown in FIG. 3 of the disclosure.

3 . A method of isolating Phorbol (2) from Croton tiglium seeds, the method comprising the steps of:

(a) pulverizing Croton tiglium seeds;

(b) extracting the pulverized seeds by refluxing with methanol and concentrating the product thereof to an oil;

(c) extracting the oil with a plurality of methanol washes and pooling the methanol washes;

(d) adding cesium carbonate to the methanol washes with prolonged stirring

(e) acidifying the product of the preceding step with 6M sulfuric acid to a pH of 5.5;

(f) filtering the acidified product and concentrating the filtrate therefrom under reduced pressure at 30° C.;

(g) saturating the aqueous suspension from step (f) sodium chloride;

(h) washing the aqueous phase with diethyl ether;

(i) extracting the diethyl ether with tetrahydrofuran (THF) and concentrating the THF extract under reduced pressure at 30° C.; drying the THF extract concentrate and purifying by silica gel vacuum column chromatography.

Assignments (1)

Continuity (2)

References Cited (80)