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A Stereoselective Aldol Approach for the Total Syntheses of Two 6‐Alkylated 2 H ‐Pyran‐2‐ones
Author(s) -
Rajaram Singanaboina,
Ramesh Dasari,
Ramulu Udugu,
Prabhakar Peddikotla,
Venkateswarlu Yenamandra
Publication year - 2014
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201300139
Subject(s) - chemistry , stereoselectivity , aldol reaction , alkylation , pyran , olefin fiber , total synthesis , olefin metathesis , metathesis , stereochemistry , organic chemistry , catalysis , polymerization , polymer
Abstract A simple and highly efficient stereoselective total synthesis of the 6‐alkylated pyranones (6 R )‐6‐[(1 E ,4 R ,6 R )‐4,6‐dihydroxy‐10‐phenyldec‐1‐en‐1‐yl]‐5,6‐dihydro‐2 H ‐pyran‐2‐one ( 1 ) and (6 S )‐5,6‐dihydro‐6‐[(2 R )‐2‐hydroxy‐6‐phenylhexyl]‐2 H ‐pyran‐2‐one ( 2 ) was developed using Crimmins ' aldol reaction, SmI 2 reduction, Grubbs ‐ II ‐catalyzed olefin cross‐metathesis, and Still 's modified Horner Wadsworth Emmons reaction.