Formal Synthesis of Premisakinolide A and C(19)–C(32) of Swinholide A via Site-Selective C–H Allylation and Crotylation of Unprotected Diols

Formal Synthesis of Premisakinolide A and C(19)–C(32) of Swinholide A via Site-Selective C–H Allylation and Crotylation of Unprotected Diols

Using stereo- and site-selective C–H allylation and crotylation of unprotected diols, an intermediate in the synthesis of premisakinolide A (bistheonellic acid B) that was previously made in 16–27 (LLS) steps is now prepared in only nine steps. This fragment also represents a synthesis of C(19)–C(32...

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Veröffentlicht in:Organic letters 2015-10, Vol.17 (19), p.4686-4689
Hauptverfasser: Shin, Inji, Krische, Michael J
Format: Artikel
Sprache:eng
Schlagworte:
Actins - metabolism
Alcohols - chemistry
Catalysis
Macrolides - chemical synthesis
Macrolides - chemistry
Marine Toxins - chemical synthesis
Marine Toxins - chemistry
Molecular Structure
Stereoisomerism
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Zusammenfassung:Using stereo- and site-selective C–H allylation and crotylation of unprotected diols, an intermediate in the synthesis of premisakinolide A (bistheonellic acid B) that was previously made in 16–27 (LLS) steps is now prepared in only nine steps. This fragment also represents a synthesis of C(19)–C(32) of the actin-binding macrodiolide swinholide A.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b02056