Total Synthesis of Myceliothermophins C, D, and E

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...

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Bibliographic Details
Published in:	Angewandte Chemie International Edition Vol. 53; no. 41; pp. 10970 - 10974
Main Authors:	Nicolaou, K. C., Shi, Lei, Lu, Min, Pattanayak, Manas R., Shah, Akshay A., Ioannidou, Heraklidia A., Lamani, Manjunath
Format:	Journal Article
Language:	English
Published:	Weinheim WILEY-VCH Verlag 06-10-2014 WILEY‐VCH Verlag
Subjects:	Biological Products - chemical synthesis Biological Products - chemistry cascade reactions Crystallography, X-Ray Cyclization decalin Molecular Conformation Naphthalenes - chemistry natural products Nitrobenzoates - chemistry polyketides Polyketides - chemical synthesis Polyketides - chemistry Stereoisomerism total synthesis cascade reactions natural products decalin total synthesis polyketides
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Summary:	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. Cascades: The total synthesis of the cytotoxic myceliothermophins C, D, and E have been achieved through a sequence involving a cascade bis(cyclization) of epoxide or aldehyde substrates to forge a trans‐fused decalin precursor of the natural products.
Bibliography:	Bristol-Myers Squibb ArticleID:ANIE201406815 Rice University istex:57311F5D32400C422835D3216935C33F73695CEC National Institutes of Health - No. AI0055475 ark:/67375/WNG-TK3FCNJH-3 The Cancer Prevention & Research Institute of Texas (CPRIT) European Commission Financial support was provided by The Cancer Prevention & Research Institute of Texas (CPRIT), the National Institutes of Health (USA) (grant AI0055475), the National Science Foundation, and Rice University. Fellowships to M. Lu (Bristol-Myers Squibb) and H.A.I. (Marie-Curie International Outgoing Fellowship, European Commission) are gratefully acknowledged. National Science Foundation Financial support was provided by The Cancer Prevention & Research Institute of Texas (CPRIT), the National Institutes of Health (USA) (grant AI0055475), the National Science Foundation, and Rice University. Fellowships to M. Lu (Bristol‐Myers Squibb) and H.A.I. (Marie‐Curie International Outgoing Fellowship, European Commission) are gratefully acknowledged. ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.201406815