SYNTHETIC STUDIES OF HALICHONDRIN-B, AN ANTITUMOR POLYETHER MACROLIDEISOLATED FROM A MARINE SPONGE .6. SYNTHESIS OF THE C1-C15 UNIT VIA STEREOSELECTIVE CONSTRUCTION OF THE B-RING AND A-RING BY KINETICALLY ANDTHERMODYNAMICALLY CONTROLLED MICHAEL-REACTIONS WITH THE AID OF COMPUTATIONAL SEARCH FOR DOMINANT CONFORMERS

Authors
HORITA K HACHIYA S YAMAZAKI T NAITOU T UENISHI J YONEMITSU O
Citation
K. Horita et al., SYNTHETIC STUDIES OF HALICHONDRIN-B, AN ANTITUMOR POLYETHER MACROLIDEISOLATED FROM A MARINE SPONGE .6. SYNTHESIS OF THE C1-C15 UNIT VIA STEREOSELECTIVE CONSTRUCTION OF THE B-RING AND A-RING BY KINETICALLY ANDTHERMODYNAMICALLY CONTROLLED MICHAEL-REACTIONS WITH THE AID OF COMPUTATIONAL SEARCH FOR DOMINANT CONFORMERS, Chemical and Pharmaceutical Bulletin, 45(8), 1997, pp. 1265-1281
Citations number
33
Categorie Soggetti
Pharmacology & Pharmacy",Chemistry
Journal title
Chemical and Pharmaceutical Bulletin → ACNP
ISSN journal
00092363
Volume
45
Issue
8
Year of publication
1997
Pages
1265 - 1281
Database
ISI
SICI code
0009-2363(1997)45:8<1265:SSOHAA>2.0.ZU;2-H
Abstract
The C1-C15 unit of halichondrin B was synthesized starting from D-gluc ose via stereoselective construction of the B and A rings, which have 2,6-trans-and 2,6-cis-disubstituted tetrahydropyran rings, respectivel y, With the aid of MM2 calculations kinetically and thermodynamically controlled Michael reactions were successfully applied for the constru ction of the B and A rings, respectively.