Synthesis of Portentol

Erick M. Carreira; Leonardo J. Nannini

doi:10.1055/s-0035-1561001

RSS-Feed abonnieren

Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.

https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000131.xml

Teilen / Bookmarken

Facebook Linkedin Weibo

PDF herunterladen

Synfacts 2016; 12(1): 0003
DOI: 10.1055/s-0035-1561001

Synthesis of Natural Products and Potential Drugs

Synthesis of Portentol

Rezensent(en):

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

Crossref PubMed Suche in Google Scholar

Weitere Informationen

Publikationsverlauf

Publikationsdatum:
16. Dezember 2015 (online)

Abstract
Volltext
Abbildungen

als PDF herunterladen Lizenzen und Reprints

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.

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.

Lizenzen und Reprints