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Chemistry and Stereochemistry of Iridoids, X. Enantiomerically Pure Hexahydropentalene Derivatives – Building Units for the Synthesis of Cyclopentanoid Natural Products
Author(s) -
Weinges Klaus,
Haremsa Sylke
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.198719870807
Subject(s) - chemistry , catalpol , iridoid , stereochemistry , absolute configuration , resolution (logic) , total synthesis , organic chemistry , glucoside , glycoside , medicine , alternative medicine , pathology , artificial intelligence , computer science
The synthesis of the enantiomerically pure hexahydropentalene derivatives 5a–5e starting from the iridoid glucoside catalpol is described. The absolute configuration reported for (1α,3aβ,6aβ)‐1,2,3,3a,4,6a‐hexahydro‐1‐pentalenol ( 5d ), which has been obtained by optical resolution, is confirmed by preparation of the crystalline camphanate 5e .