Radical-Based Asymmetric Synthesis:
An Iterative Approach to 1, 3, 5, ...
(2<i>n</i> + 1) Polyols
Philip Garner
James T. Anderson
10.1021/ol990188v.s001
https://acs.figshare.com/articles/journal_contribution/Radical-Based_Asymmetric_Synthesis_An_Iterative_Approach_to_1_3_5_2_i_n_i_1_Polyols/3759753
A conceptually novel approach to 1, 3, 5, ... (2<i>n</i><i> </i>+ 1) polyols based on iterative stereocontrolled homologation of chiral hydroxyalkyl radicals
is reported. Starting from α-keto ester precursors, the general sequence of (1) ketone reduction, (2) auxiliary attachment, (3) saponification,
(4) Barton esterification, and (5) radical addition provided the two-carbon homologue in 70−80% overall yield. The simplicity and generality of
this iterative strategy for 1, 3, 5, ... (2<i>n</i><i> </i>+ 1) polyol synthesis suggests an attractive alternative for the preparation of molecules containing this
structural motif.
1999-09-04 00:00:00
homologue
molecule
iterative stereocontrolled homologation
sequence
novel approach
generality
alternative
Barton
Asymmetric
saponification
attachment
iterative strategy
polyols
ester
Synthesi
simplicity
chiral hydroxyalkyl radicals
Iterative Approach
esterification
keto
Polyol
precursor
motif
preparation
ketone
polyol
synthesis