Asymmetric Synthesis of the Northern Half C1−C16 of the Bryostatins

Asymmetric Synthesis of the Northern Half C1−C16 of the Bryostatins

Starting from 8-oxabicyclo[3.2.1]oct-6-en-3-one and racemic 2,2-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one, the C1−C16 segment of the bryostatins has been synthesized in 30 steps and 9% overall yield (17 steps longest linear sequence). Fragment coupling by dithiane strategy and protecting group mani...

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Veröffentlicht in:Organic letters 2001-03, Vol.3 (6), p.929-932
Hauptverfasser: Vakalopoulos, A, Lampe, T. F. J, Hoffmann, H. M. R
Format: Artikel
Sprache:eng
Schlagworte:
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Bryostatins
Indicators and Reagents
Lactones - chemical synthesis
Lactones - chemistry
Macrolides
Models, Molecular
Molecular Conformation
Molecular Structure
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Zusammenfassung:Starting from 8-oxabicyclo[3.2.1]oct-6-en-3-one and racemic 2,2-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one, the C1−C16 segment of the bryostatins has been synthesized in 30 steps and 9% overall yield (17 steps longest linear sequence). Fragment coupling by dithiane strategy and protecting group manipulations provided an advanced chemodifferentiated northern half segment.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol015551o