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Synthetic Studies towards Pseurotin A. Part 3. Synthesis of a related highly functionalized γ‐lactone
Author(s) -
Su Zhuang,
Tamm Christoph
Publication year - 1995
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19950780518
Subject(s) - chemistry , lactone , stereochemistry , combinatorial chemistry , organic chemistry
A new general concept for the total synthesis of pseurotin A ( 1 ), a secondary metabolite of Pseudeurotium ovalis S TOLK , which possesses a highly substituted 1‐oxa‐7‐azaspiro[4.4]nonane skeleton, is presented. A key intermediate of the planned reaction sequence is the functionalized γ‐lactone 8 . The corresponding protected compound 52 was prepared using ( S )‐ O , O ‐isopropylideneglyceraldehyde ( 13 ) and the bromoacetal 14 as starting material. γ‐Lactone 52 was obtained in enantiomerically pure state in ten steps. It possesses the desired configuration.