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Total Synthesis of (−)‐(3 S ,6 R )‐3,6‐Dihydroxy‐10‐methylundecanoic Acid and Its Trimer
Author(s) -
ZHANG XianShu,
DA ShiJun,
JIAO Yang,
LI HuiZhi,
XIE ZhiXiang,
LI Ying
Publication year - 2008
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200890239
Subject(s) - trimer , chemistry , yield (engineering) , total synthesis , stereochemistry , organic chemistry , dimer , thermodynamics , physics
The asymmetric total synthesis of (3 S ,6 R )‐3,6‐dihydroxy‐10‐methylundecanoic acid and its trimer was accomplished from commercially available 1‐bromo‐3‐methylbutane in 11 steps in a 27.5% overall yield and 14 steps in a 24.5% overall yield, respectively. The key steps were asymmetric allylboration via allyldiisopinocampheylborane and Yamaguchi's esterification reaction.