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Synthetic Studies Directed toward the Pseurotins. Part I. Synthesis of Related Furan‐3(2 H )‐ones
Author(s) -
Dolder Matthys,
Shao Xie,
Tamm Christoph
Publication year - 1990
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.19900730106
Subject(s) - chemistry , furan , aldehyde , ketone , moiety , aldol condensation , aldol reaction , total synthesis , stereochemistry , metabolite , organic chemistry , catalysis , biochemistry
According to a general concept for the total synthesis of pseurotin A ( 1 ), a secondary metabolite of Pseudeurotium ovalis S TOLK , 5‐[(1 S ,2 S , Z )‐1,2‐dihydroxyhex‐3‐enyl]‐2,2,4‐trimethylfuran‐3(2 H )‐one ( 17 ) was prepared. It is a model substance for the substituted furan‐3(2 H )‐one moiety of 1 . The aldol condensation of the aldehyde 26 , derived from D‐glucose, and the enolate of ketone 29 served as key reaction.