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Studies Directed toward the Synthesis of Phomenoic Acid. Part 1. Enantioselective synthesis of the C(1)‐to‐C(6) segment
Author(s) -
Hassan Hammed H. A. M.,
Tamm Christoph
Publication year - 1994
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.19940770323
Subject(s) - synthon , chemistry , enantiomer , enantioselective synthesis , retrosynthetic analysis , stereochemistry , formal synthesis , combinatorial chemistry , total synthesis , organic chemistry , catalysis
Based on a retrosynthetic analysis, a concept for the synthesis of all stereoisomers of the C(1)‐to‐C(6) segment of phomenoic acid has been developed. Both enantiomers of the chiral synthon 9 were prepared starting from rac ‐epoxy‐diester 10 . They were converted to both enantiomers of the epoxyalcohol, 16 and 21 , respectively, using Sharpless epoxydation. They served as building blocks for the synthesis of the tetrol derivatives 20 and 22 , respectively. All four stereoisomers were obtained in optically pure form. They contain the correct assembly of protected functional groups, allowing selective deprotection in view of further transformations.