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Total Synthesis of (+)‐Colletodiol from ( S,S )‐Tartrate and ( R )‐3‐Hydroxybutanoate
Author(s) -
Schnurrenberger Peter,
Hungerbühler Ernst,
Seebach Dieter
Publication year - 1987
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198719870821
Subject(s) - tartrate , yield (engineering) , chemistry , total synthesis , stereochemistry , medicinal chemistry , organic chemistry , physics , thermodynamics
The macrodiolide antibiotic (+)‐colletodiol (7, Scheme 1) was synthesised. The configuration was thus proven to be (6 R ,11 R ,12 R ,14 R ). – Key intermediates (Schemes 9 and 10) are the two hydoxy acids 43 and 64 , which were prepared from dimethyl ( S,S )‐tartrate in 20% overall yield (12 steps) and from ( R )‐3‐hydroxybutanoate in 57% overall yield (6 steps), respectively. The two hydroxy acids were cyclised to give, after deprotection, the title compound. – Our investigations led to the production of a large number of chiral building blocks, many of them in different stereoisomeric forms.