The total synthesis of (+)-tedanolide - A macrocyclic polyketide from marine sponge tedania ignis

authored by

Gunnar Ehrlich, Jorma Hassfeld, Ulrike Eggert, Markus Kalesse

Abstract

Tedanolide, which was isolated by Schmitz in 1984 from the marine sponge Tedania ignis, is a highly cytotoxic macrolide leading to strong growth inhibition of P338 tumor cells in bioassays. A unique structural feature of the known tedanolides is the primary hydroxyl group incorporated in the macrolactone. This unusual motif for macrolactones originated from PKS biosynthesis might arise through lactonizations others than those derived by the thioesterase reaction. First experimental data that support this hypothesis and reflect the inherent preference of PKS-induced macrolactonization were obtained during this synthesis. The inherent preference for the formation of a 14-membered macrocyclization is discussed together with the pivotal steps in the synthesis.

Organisation(s)

Institute of Organic Chemistry

Type

Article

Journal

Chemistry - a European journal

Volume

14

Pages

2232-2247

No. of pages

16

ISSN

0947-6539

Publication date

27.02.2008

Publication status

Published

Peer reviewed

Yes

ASJC Scopus subject areas

Catalysis, Organic Chemistry

Sustainable Development Goals

SDG 14 - Life Below Water

Electronic version(s)

https://doi.org/10.1002/chem.200701529 (Access: Unknown)