Cover Picture: Generation of (+)‐Prezizanol, (+)‐Prezizaene, and the ent‐β‐Isopipitzol Framework via Cationic Rearrangement of Khusiol and Related Compounds (Asian J. Org. Chem. 5/2014). Issue 5 (May 2014)

• Record Type: Journal Article
• Authors: Sharma, Mukesh K.; Banwell, Martin G.; Willis, Anthony C.
• Is Part Of: Asian journal of organic chemistry. Volume 3:Issue 5(2014:May)
• Page Start: 569
• Page End: 569
• Publication Date: 2014-05
• Subjects: Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201490008
• Languages: English
• ISSNs: 2193-5807

Abstract

<abstract abstract-type="graphical" xml:lang="en"> <title> <x xml:space="preserve">Abstract</x> </title> <p> <bold>The chemoenzymatically derived</bold> khusiol framework can be engaged in two quite distinct (divergent) Wagner–Meerwein rearrangement reactions depending on the associated functionality. In their Full Paper on <ext-link ext-link-type="doi" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">page 632 ff., </ext-link> Martin Banwell and co‐workers show that in the first of these reactions, POCl₃ effects the smooth conversion of <italic>epi</italic>‐khusiol into (+)‐prezizaene, a key component of the important perfumery ingredient vetiver oil. In the second, a cyclic sulfate embedded within the khusiol framework rearranges to a very pleasant smelling tricyclic alcohol that is part of the previously unreported <italic>ent</italic>‐β‐isopipitzol framework. Cover art produced by Ingrid Banwell.<boxed-text content-type="graphic" position="anchor" orientation="portrait"><graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgh58v9hp" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /></boxed-text></p> </abstract>