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Espicufolin

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Category Others
Catalog number BBF-00871
CAS 182232-96-8
Molecular Weight 378.37
Molecular Formula C22H18O6

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Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

Fermentation Plant

Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

Espicufolin is a neuroprotective agent produced by Streptomyces sp. cu39.

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Synonyms 2-[(2R)-butan-2-yl]-11-hydroxy-5-(hydroxymethyl)-4H-naphtho[2,3-h]chromene-4,7,12-trione; (R)-Espicufolin
IUPAC Name 2-[(2R)-butan-2-yl]-11-hydroxy-5-(hydroxymethyl)naphtho[2,3-h]chromene-4,7,12-trione
Canonical SMILES CCC(C)C1=CC(=O)C2=C(O1)C3=C(C=C2CO)C(=O)C4=C(C3=O)C(=CC=C4)O
InChI InChI=1S/C22H18O6/c1-3-10(2)16-8-15(25)17-11(9-23)7-13-19(22(17)28-16)21(27)18-12(20(13)26)5-4-6-14(18)24/h4-8,10,23-24H,3,9H2,1-2H3/t10-/m1/s1
InChI Key HXAZTNIVBVVFJS-SNVBAGLBSA-N
Appearance Yellow Powder
Melting Point 184-186°C
Solubility Soluble in Methanol, methyl ether, ethyl acetate
1. Novel strategies for the synthesis of anthrapyran antibiotics: discovery of a new antitumor agent and total synthesis of (S)-espicufolin
Lutz F Tietze, Kersten M Gericke, Ramakrishna Reddy Singidi, Ingrid Schuberth Org Biomol Chem. 2007 Apr 21;5(8):1191-200. doi: 10.1039/b700838d. Epub 2007 Mar 14.
Two high-yielding strategies for the synthesis of 4H-anthra[1,2-b]pyran antibiotics have been developed giving access to novel antitumor agent (ED(50) 1.5 microm) and to (S)-espicufolin (3). A key step for the assembly of the tetracyclic 4H-anthra[1,2-b]pyran-4,7,12-trione skeleton is the nucleophilic addition of an aryl lithium species onto an aldehyde which allows the introduction of either an ynone or 1,3-diketo side chain, serving as precursors for an acid-catalysed cyclisation.

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