Total Synthesis of Myceliothermophins C, D, and E | Zendy

Nicolaou K. C. | Zendy; Shi Lei | Zendy; Lu Min | Zendy; Pattanayak Manas R. | Zendy; Shah Akshay A. | Zendy; Ioannidou Heraklidia A. | Zendy; Lamani Manjunath | Zendy

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Total Synthesis of Myceliothermophins C, D, and E

Author(s) -

Nicolaou K. C.,

Shi Lei,

Lu Min,

Pattanayak Manas R.,

Shah Akshay A.,

Ioannidou Heraklidia A.,

Lamani Manjunath

Publication year - 2014

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201406815

Subject(s) - total synthesis , stereochemistry , enantiomer , chemistry , cascade , decalin , stereocenter , enantioselective synthesis , organic chemistry , chromatography , catalysis

The total synthesis of cytotoxic polyketides myceliothermophins E ( 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.

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