Total Synthesis of MyceliothermophinsC, D, and E

Total Synthesis of MyceliothermophinsC, D, and E

The total synthesis of cytotoxic polyketides myceliothermophinsE (1), C (2), and D (3) through a cascade-based cyclization to form the trans-fused decalin system is described. The convergent synthesis delivered all three natural products through late-stage divergence and facilitated unambiguous C21...

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Veröffentlicht in:Angewandte Chemie 2014-10, Vol.126 (41), p.11150-11154
Hauptverfasser: Nicolaou, K C, Shi, Lei, Lu, Min, Pattanayak, Manas R, Shah, Akshay A, Ioannidou, Heraklidia A, Lamani, Manjunath
Format: Artikel
Sprache:eng ; ger
Schlagworte:
Chemistry
Crystallography
Decalin
Divergence
Natural products
Synthesis
X-rays
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Zusammenfassung:The total synthesis of cytotoxic polyketides myceliothermophinsE (1), C (2), and D (3) through a cascade-based cyclization to form the trans-fused decalin system is described. The convergent synthesis delivered all three natural products through late-stage divergence and facilitated unambiguous C21 structural assignments for 2 and 3 through X-ray crystallographic analysis, which revealed an interesting dimeric structure between its enantiomeric forms. [PUBLICATION ABSTRACT]
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201406815