Synthetic studies of halichondrin B, an antitumor polyether macrolide isolated from a marine sponge. 6. Synthesis of the C1 - C15 unit via stereoselective construction of the B and A rings by kinetically and thermodynamically controlled Michael reactions with the aid of computational search for dominant conformers

DOI: 10.1248/cpb.45.1265

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Chemical and Pharmaceutical Bulletin p. 1265 - 1281 (1997)

Update date:2022-08-03

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Authors:

Horita, Kiyoshi

Hachiya, Shun-Ichiro

Yamazaki, Tatsuya

Naitou, Tae

Uenishi, Jun'ichi

Yonemitsu, Osamu

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Article abstract of DOI:10.1248/cpb.45.1265

The C1 - C15 unit of halichondrin B was synthesized starting from D- glucose via stereoselective construction of the B and A rings, which have 2,6-trans- and 2,6-cis-disubstituted tetrahydropyran rings, respectively. With the aid of MM2 calculations kinetically and thermodynamically controlled Michael reactions were successfully applied for the construction of the B and A rings, respectively.

Full text of DOI:10.1248/cpb.45.1265

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DOI: 10.1248/cpb.45.1265