Highly Functionalized Pyranopyrans from Furans: A Synthesis of the C27−C38 and C44−C53 Subunits of Norhalichondrin B
- 14 November 2007
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 9 (25) , 5299-5302
- https://doi.org/10.1021/ol702559e
Abstract
A synthesis of highly functionalized pyranopyrans based on an Achmatowicz oxidation followed by a remarkably diastereoselective Kishi reduction is described in the context of studies directed toward norhalichondrin B.Keywords
This publication has 35 references indexed in Scilit:
- Structurally simplified macrolactone analogues of halichondrin BBioorganic & Medicinal Chemistry Letters, 2004
- Antitumor Polyether Macrolides: New and Hemisynthetic Halichondrins from the New Zealand Deep-Water Sponge Lissodendoryx sp.The Journal of Organic Chemistry, 1997
- Enantioselective synthesis of a halichondrin B C(20)→C(36) precursorTetrahedron Letters, 1995
- An expeditious synthesis of the C(1)-C(14) subunit of halichondrin BTetrahedron Letters, 1994
- : Isolation and structure of halistatin 1 from the eastern Indian Ocean marine sponge Phakellia carteriThe Journal of Organic Chemistry, 1993
- Total synthesis of halichondrin B and norhalichondrin BJournal of the American Chemical Society, 1992
- Synthesis of a C(22)a˚C(34) halichondrin precursor via a double dioxanone-to-dihydropyran rearrangementTetrahedron Letters, 1991
- Synthetic studies towards halichondrinsTetrahedron Letters, 1987
- Halichondrins - antitumor polyether macrolides from a marine spongePure and Applied Chemistry, 1986
- Norhalichondrin A: an antitumor polyether macrolide from a marine spongeJournal of the American Chemical Society, 1985