Nucleophilic addition of organozinc reagents to 2-sulfonyl cyclic ethers: stereoselective synthesis of manassantins A and B.
Org Lett
; 11(1): 89-92, 2009 Jan 01.
Article
in En
| MEDLINE
| ID: mdl-19111058
ABSTRACT
A convergent route to the synthesis of manassantins A and B, potent inhibitors of HIF-1, is described. Central to the synthesis is a stereoselective addition of an organozinc reagent to a 2-benzenesulfonyl cyclic ether to achieve the 2,3-cis-3,4-trans-4,5-cis-tetrahydrofuran of the natural products. Preliminary structure-activity relationships suggested that the (R)-configuration at C-7 and C-7''' is not critical for HIF-1 inhibition. In addition, the hydroxyl group at C-7 and C-7''' can be replaced with a carbonyl group without loss of activity.
Full text:
1
Database:
MEDLINE
Main subject:
Organometallic Compounds
/
Sulfones
/
Zinc
/
Lignans
/
Ethers, Cyclic
/
Furans
Language:
En
Year:
2009
Type:
Article