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The Synthesis of Boronolide
Author(s) -
Jefford Charles W.,
Moulin MarieClaude
Publication year - 1991
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.19910740213
Subject(s) - chemistry , acrolein , allylic rearrangement , yield (engineering) , hydroxylation , acetylation , silylation , dimer , allylic alcohol , alcohol , medicinal chemistry , diastereomer , organic chemistry , stereochemistry , catalysis , biochemistry , materials science , metallurgy , gene , enzyme
Racemic boronolide ( 1 ) is prepared in six steps in 4.4% overall yield from acrolein dimer 6 and 1‐(trimethyl‐silyl)hex‐1‐yne ( 8 ). The latter, by hydromagnesiation, is condensed with 6 to give the corresponding threo ‐allylic alcohol 13 ( Scheme 2 ). Conversion of 13 to the erythro ‐allylic alcohol 5 ( Scheme 3 ), bis‐hydroxylation, and acetylation afford 1 .
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