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Synthesis 2009(18): 3061-3066
DOI: 10.1055/s-0029-1216918
DOI: 10.1055/s-0029-1216918
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Studies on the C22-C23 Aldol Coupling of Spirangien
Weitere Informationen
Received
5 March 2009
Publikationsdatum:
23. Juli 2009 (online)
Publikationsverlauf
Publikationsdatum:
23. Juli 2009 (online)
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Abstract
The aldol reaction is one of the most powerful and versatile methods in polyketide synthesis. Nevertheless, the subtle directing effects remain very often obscure and impede complex natural products syntheses. Here, we report studies on the pivotal aldol coupling employed in the spirangien synthesis. We identified conditions for the stereoselective formation of both stereoisomers in the C22-C23 aldol juncture of spirangien.
Key words
aldol reaction - methyl ketone - natural products - 1,4-induction - Felkin product - Cornforth model
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