A Stereoselective Aldol Approach for the Total Syntheses of Two 6‐Alkylated 2H‐Pyran‐2‐ones. Issue 1 (January 2014)

• Record Type: Journal Article
• Authors: Rajaram, Singanaboina; Ramesh, Dasari; Ramulu, Udugu; Prabhakar, Peddikotla; Venkateswarlu, Yenamandra
• Is Part Of: Helvetica chimica acta. Volume 97:Issue 1(2014:Jan.)
• Page Start: 112
• Page End: 121
• Publication Date: 2014-01
• Subjects: Chemistry -- Periodicals; Chemistry, Analytical -- periodicals; Chimie -- Périodiques; 540
• DOI: 10.1002/hlca.201300139
• Languages: English
• ISSNs: 0018-019X

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>A simple and highly efficient stereoselective total synthesis of the 6‐alkylated pyranones (6<italic>R</italic>)‐6‐[(1<italic>E</italic>, 4<italic>R</italic>, 6<italic>R</italic>)‐4, 6‐dihydroxy‐10‐phenyldec‐1‐en‐1‐yl]‐5, 6‐dihydro‐2<italic>H</italic>‐pyran‐2‐one (<bold>1</bold>) and (6<italic>S</italic>)‐5, 6‐dihydro‐6‐[(2<italic>R</italic>)‐2‐hydroxy‐6‐phenylhexyl]‐2<italic>H</italic>‐pyran‐2‐one (<bold>2</bold>) was developed using <italic>Crimmins</italic>' aldol reaction, SmI₂ reduction, <italic>Grubbs</italic>‐<italic>II</italic>‐catalyzed olefin cross‐metathesis, and <italic>Still</italic>'s modified <italic>Horner</italic><italic>Wadsworth</italic><italic>Emmons</italic> reaction.</p> </abstract>