Synthetic Studies of Halichondrin B, an Antitumor Polyether Macrolide Isolated from a Marine Sponge. 1. Stereoselective Synthesis of the C1-C13 Fragment via Construction of the B and A Rings by Kinetically and thermodynamically Controlled Intramolecular Michael Reactions.

Kiyoshi Horita,S. Hachiya,Masaaki Nagasawa,Masataka Hikota,Osamu Yonemitsu

Synthetic Studies of Halichondrin B, an Antitumor Polyether Macrolide Isolated from a Marine Sponge. 1. Stereoselective Synthesis of the C1-C13 Fragment via Construction of the B and A Rings by Kinetically and thermodynamically Controlled Intramolecular Michael Reactions.

1994

Kiyoshi Horita
S. Hachiya
Masaaki Nagasawa
Masataka Hikota
Osamu Yonemitsu

A stereoselective synthesis of the C1-C13 fragment of halichondrin B starting from D-glucose is reported. Construction of 2,5-trans (B) and 2,5-cis substituted tetrahydropyran (A) rings using intramolecular Michael reactions under kinetical and thermodynamical conditions, respectively, were the critical steps.

Keywords:

Organic chemistry
Stereochemistry
Aldose
Intramolecular reaction
Halichondrin B
Intramolecular force
Stereoselectivity
Tetrahydropyran
Chemistry
Michael reaction
Sponge

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