Issue 28, 2024

Total synthesis and structure–antifouling activity relationship of scabrolide F

Abstract

An efficient synthetic strategy for scabrolide F (7), a norcembranolide diterpene that was isolated from the Taiwanese soft coral Sinularia scabra, has only recently been reported by our group. Herein, we report details of the first total synthesis of 7. The tetrahydrofuran domain of 7 was stereoselectively constructed via the 5-endo-tet cyclization of a hydroxy vinyl epoxide. The reaction of alkyl iodide 30 with dithiane 38, followed by the introduction of an alkene moiety, afforded allylation precursor 41. The coupling of alkyl iodide 42 and allylic stannane 43 was examined as a model experiment of allylation. Because the desired allylated product 44 was not obtained, an alternative synthetic route toward 7 was investigated instead. In the second synthetic approach, fragment–coupling between alkyl iodide 56 and aldehyde 58, macrolactonization, and transannular ring-closing metathesis were used as the key steps to achieve the first total synthesis of 7. We hope that this synthetic strategy provides access to the total synthesis of other macrocyclic norcembranolides. We also evaluated the antifouling activity and toxicity of 7 and its synthetic intermediates toward the cypris larvae of the barnacle Amphibalanus amphitrite. This study is the first to report the antifouling activity of norcembranolides as well as the biological activity of 7.

Graphical abstract: Total synthesis and structure–antifouling activity relationship of scabrolide F

Supplementary files

Article information

Article type
Paper
Submitted
30 Apr 2024
Accepted
23 May 2024
First published
23 May 2024
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2024,22, 5739-5747

Total synthesis and structure–antifouling activity relationship of scabrolide F

H. Takamura, Y. Sugitani, R. Morishita, T. Yorisue and I. Kadota, Org. Biomol. Chem., 2024, 22, 5739 DOI: 10.1039/D4OB00698D

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements