Synthetic studies of halichondrin B, an antitumor polyether macrolide isolated from a marine sponge. 7. Synthesis of two C27-C36 units via construction of the F ring and completely stereoselective C-glycosylation using mixed Lewis acids

DOI: 10.1248/cpb.45.1558

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 1558 - 1572 (1997)

Update date:2022-08-03

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Authors:

Horita, Kiyoshi

Sakurai, Youji

Nagasawa, Masaaki

Yonemitsu, Osamu

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Article abstract of DOI:10.1248/cpb.45.1558

Two C27-C36 units of halichondrin B were synthesized starting from a C31-C34 alcohol, which was easily available from dimethyl L-tartrate, via construction of the F ring, methylation at the C31 position and C- glycosylation. These crucial reactions proceeded completely stereoselectively, and in particular the stereoselective C-glycosylation with allyltrimethylsilane took place only in the presence of both of two Lewis acids, boron trifluoride etherate and trimethylsilyl triflate.

Full text of DOI:10.1248/cpb.45.1558

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