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Synfacts 2016; 12(1): 0003
DOI: 10.1055/s-0035-1561001
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Portentol

Contributor(s):
Erick M. Carreira
,
Leonardo J. Nannini
Cheng B, Trauner D * Ludwig-Maximilians-Universität München, Germany
A Highly Convergent and Biomimetic Total Synthesis of Portentol.

J. Am. Chem. Soc. 2015;
137: 13800-13803
CrossrefPubMedSearch in Google Scholar
Further Information

Publication History

Publication Date:
16 December 2015 (online)

 
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Key words

biomimetic synthesis - Evans aldol reaction - polyketide - portentol

Significance

Cheng and Trauner report the asymmetric total synthesis of the polyketide portentol, isolated in 1967 from lichen Roccella Portentosa. The synthesis relies on a cascade sequence, mimicking the hypothetical biosynthesis.


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Comment

Fragment C was synthesized by means of an Evans aldol reaction. Oxidation of the primary alcohol, followed by aldol reaction with ketone G and deprotection, gave lactone H, which underwent oxidation, oxonium ion formation, and aldol reaction upon treatment with DMSO and TFAA.


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