Synthetic study of andrastins: stereoselective construction of the BCD-ring system

Andrastins are meroterpenes isolated from Penicillium sp. FO-3929 that display highly potent inhibitory activities toward protein farnesyltransferase. Structurally, they possess a unique steroidal tetracyclic skeleton (the ABCD-ring) with three contiguous quaternary stereocenters on the C-ring. Here...

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Bibliographic Details
Published inJournal of antibiotics Vol. 72; no. 6; pp. 384 - 388
Main Authors Yoshimura, Fumihiko, Abe, Taiki, Ishioka, Yuichi, Tanino, Keiji
Format Journal Article
LanguageEnglish
Published London Nature Publishing Group UK 01.06.2019
Springer Nature
Nature Publishing Group
Subjects
639/638/403/977
639/638/549/933
Bacteriology
Biomedical and Life Sciences
Bioorganic Chemistry
Biotechnology & Applied Microbiology
Immunology
Life Sciences
Life Sciences & Biomedicine
Medicinal Chemistry
Microbiology
Organic Chemistry
Pharmacology & Pharmacy
Saturn
Science & Technology
Special Feature: Article
PENICILLIUM SP FO-3929
PROTEIN FARNESYLTRANSFERASE INHIBITORS
DIELS-ALDER
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Summary:Andrastins are meroterpenes isolated from Penicillium sp. FO-3929 that display highly potent inhibitory activities toward protein farnesyltransferase. Structurally, they possess a unique steroidal tetracyclic skeleton (the ABCD-ring) with three contiguous quaternary stereocenters on the C-ring. Herein, we describe our nitrile cyclization-based approach to the stereoselective construction of the BCD-ring system of andrastins, which contains three contiguous quaternary stereocenters on the C-ring and the correct oxidation states of the D-ring.
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ISSN:0021-8820
1881-1469
DOI:10.1038/s41429-018-0136-x