28526-38-7

Upstream product

• 108-24-7 acetic anhydride 
• 29477-83-6 narciclasine 

Downstream Products

• 1019642-62-6 acetic acid 2,3-diacetoxy-7-O-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)-6-oxo-2,3,4,4a,5,6-hexahydro[1,3]dioxolo[4,5-j]phenanthridin-4-yl ester 
• 1019642-61-5 acetic acid 2,3-diacetoxy-7-O-(2',3',4',6'-tetra-O-benzoyl-α-D-glucopyranosyl)-6-oxo-2,3,4,4a,5,6-hexahydro[1,3]dioxolo[4,5-j]phenanthridin-4-yl ester 
• 1111106-77-4 acetic acid 3,4-diacetoxy-7-(bis-benzyloxy-phosphoryloxy)-6-oxo-2,3,4,4a,5,6-hexahydro[1,3]dioxolo[4,5-j]phenanthridin-2-yl ester 
• 1019645-88-5 acetic acid 3,4-diacetoxy-5-benzyl-7-benzyloxy-6-oxo-2,3,4,4a,5,6-hexahydro[1,3]dioxolo[4,5-j]phenanthridin-2-yl ester 
• 96281-31-1 C₁₄H₁₅NO₈ 

Relevant academic research and scientific papers

Antineoplastic agents. 550. Synthesis of 10b(S)-epipancratistatin from (+)-narciclasine

By means of a five-step reaction sequence, narciclasine (2a), isolated from Narcissus sp., was converted to 10b(S)-epipancratistatin (3a) in 5.7% overall yield. The key step entailed a radical-initiated 10b,1 C-O cleavage employing tributyltin hydride to yield a B/C cis ring juncture (3b). Biological evaluation of 10b(S)-epipancratistatin (3a) provided evidence that antineoplastic activity was reduced by a factor of 10 when the B/C trans juncture was replaced with a B/C cis ring juncture.