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An Expeditious, Non‐Iterative, and Asymmetric Synthesis of 3,5,7,9,11,13,15‐Heptahydroxypentadecanals
Author(s) -
GerberLemaire Sandrine,
Vogel Pierre
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300224
Subject(s) - chemistry , ozonolysis , polyol , ketone , stereochemistry , chain (unit) , total synthesis , organic chemistry , polyurethane , physics , astronomy
Ozonolysis of (1 R ,1′ R ,6 R ,6′ R )‐3,3′‐methylenebis{6‐[(benzyloxy)methoxy]cyclohept‐3‐en‐1‐ol} followed by the diastereoselective reduction of the resulting β‐hydroxy ketone intermediates gives a rapid route to long‐chain polyketides bearing unsymmetrical functions at their terminal positions. These can easily be converted into enantiomerically pure long‐chain 1,3‐polyol fragments. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)