Synthetic studies towards halichondrins

doi:10.1016/S0040-4039(00)96327-5

Tetrahedron Letters

Volume 28, Issue 30, 1987, Pages 3463-3466

https://doi.org/10.1016/S0040-4039(00)96327-5 Get rights and content

Abstract

An efficient, stereocontrolled route to construct the polycyclic ring system found at the C.1–C.15 moiety of halichondrins is reported.

References (14)

Y. Kishi et al.
M. Miyashita et al.
J. Org. Chem.
(1977)
D. Uemura et al.
J. Am. Chem. Soc.
(1985)
Y. Hirata et al.
Pure Appl. Chem.
(1986)
H. Jin et al.
J. Am. Chem Soc.
(1986)
K. Takai et al.
J. Am. Chem. Soc.
(1986)

There are more references available in the full text version of this article.

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Synthetic studies towards halichondrins

Abstract

J. Org. Chem.

J. Am. Chem. Soc.

Pure Appl. Chem.

J. Am. Chem Soc.

J. Am. Chem. Soc.