A Concise Total Synthesis of (+)‐Pancratistatin from D‐Glucose Featuring the Henry Reaction. Issue 4 (7th March 2013)

• Record Type: Journal Article
• Authors: Akai, Shoji; Kojima, Masaru; Yamauchi, Shunsuke; Kohji, Takahiro; Nakamura, Yutaka; Sato, Ken‐ichi
• Is Part Of: Asian journal of organic chemistry. Volume 2:Issue 4(2013:Apr.)
• Page Start: 299
• Page End: 302
• Publication Date: 2013-03-07
• Subjects: Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201300023
• Languages: English
• ISSNs: 2193-5807

Abstract

<abstract abstract-type="graphical" xml:lang="en"> <title> <x xml:space="preserve">Abstract</x> </title> <p> <bold>Sugar, oh Henry, Henry</bold>: A concise and stereoselective synthesis of (+)‐pancratistatin is described. The key nitrocyclitol compound was prepared from a <sc>D</sc>‐glucofuranose derivative with a <italic>C</italic>‐aryl group by using an intramolecular Henry reaction. The diastereoselective introduction of a <italic>C</italic>‐aryl moiety was achieved by a Michael addition of an arylcuprate to a key sugar nitroolefin.<boxed-text content-type="graphic" position="anchor" orientation="portrait"><graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgg1x45fgkc" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /></boxed-text></p> </abstract>