Highly Functionalized Pyranopyrans from Furans:  A Synthesis of the C27−C38 and C44−C53 Subunits of Norhalichondrin B

• Published in: Organic letters Vol. 9; no. 25; pp. 5299 - 5302
• Main Authors: Henderson, James A, Jackson, Katrina L, Phillips, Andrew J
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 06.12.2007; Amer Chemical Soc
• Subjects: Carbon - chemistry; Chemistry; Chemistry, Organic; Furans - chemical synthesis; Furans - chemistry; Molecular Structure; Oxidation-Reduction; Physical Sciences; Pyrans - chemical synthesis; Pyrans - chemistry; Science & Technology; HALICHONDRIN-B; EXPEDITIOUS SYNTHESIS; F-RING; STEREOSELECTIVE C-GLYCOSYLATION; EFFICIENT SYNTHESIS; CHIRAL SYNTHESIS; ANTITUMOR POLYETHER MACROLIDE; MICHAEL REACTIONS; MARINE SPONGE; NATURAL PRODUCTS

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.