Spongistatin Synthetic Studies. Evolution of a Scalable Synthesis for the EF Fragment of (+)-Spongistatin 1 Exploiting a Petasis−Ferrier Union/Rearrangement Tactic

Spongistatin Synthetic Studies. Evolution of a Scalable Synthesis for the EF Fragment of (+)-Spongistatin 1 Exploiting a Petasis−Ferrier Union/Rearrangement Tactic

An efficient, stereocontrolled, and scalable second-generation synthesis of (+)-3, an advanced EF subtarget for the total synthesis of (+)-spongistatin 1, has been achieved. Highlights of the strategy include preparation of the F-ring pyran via a Petasis−Ferrier union/rearrangement sequence and inst...

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Veröffentlicht in:Organic letters 2004-09, Vol.6 (20), p.3637-3640
Hauptverfasser: Smith, Amos B, Sfouggatakis, Chris, Gotchev, Dimitar B, Shirakami, Shohei, Bauer, David, Zhu, Wenyu, Doughty, Victoria A
Format: Artikel
Sprache:eng
Schlagworte:
Animals
Catalysis
Cyclization
Indicators and Reagents
Macrolides - analysis
Macrolides - chemical synthesis
Molecular Structure
Porifera - chemistry
Stereoisomerism
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Beschreibung
Zusammenfassung:An efficient, stereocontrolled, and scalable second-generation synthesis of (+)-3, an advanced EF subtarget for the total synthesis of (+)-spongistatin 1, has been achieved. Highlights of the strategy include preparation of the F-ring pyran via a Petasis−Ferrier union/rearrangement sequence and installation of the chlorodiene side chain employing a cyanohydrin alkylation. The longest linear sequence, 26 steps, proceeds in 8.3% overall yield.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol048418f