Synthesis Proposal of Immunosuppressive 9,10-secosteroid A from the Gorgonian Verrucella Umbraculum

Zhaocong Yuan, Hanming Li, Yining Han

2022

Abstract

The proposal of a total synthesis plan of one of a series of four biologically significant 9,10-secosteroids recently isolated from Verrucella umbraculum, together with several alternative procedures to the synthesis plan, using widely available chemicals, is described in this work. Immunosuppressive Verrucellol A is a 9,10- secosteroid with a bicyclic skeletal framework and an aromatic moiety. Herein, the reported proposal commences via the synthesis of two of the three structural constituents – the a, ß-unsaturated aryl ketone vinyl, and the olefin side chain. Later, the main bicyclic ring structure is constructed via a Robinson Annulation reaction, followed by the introduction of the olefin side chain by Grignard reductive addition. Ultimately, an epoxidation-reductive ring opening would complete the synthesis plan.

Paper Citation

in Harvard Style

Yuan Z., Li H. and Han Y. (2022). Synthesis Proposal of Immunosuppressive 9,10-secosteroid A from the Gorgonian Verrucella Umbraculum. In Proceedings of the 4th International Conference on Biomedical Engineering and Bioinformatics - Volume 1: ICBEB, ISBN 978-989-758-595-1, pages 612-619. DOI: 10.5220/0011249500003443

in Bibtex Style

@conference{icbeb22,
author={Zhaocong Yuan and Hanming Li and Yining Han},
title={Synthesis Proposal of Immunosuppressive 9,10-secosteroid A from the Gorgonian Verrucella Umbraculum},
booktitle={Proceedings of the 4th International Conference on Biomedical Engineering and Bioinformatics - Volume 1: ICBEB,},
year={2022},
pages={612-619},
publisher={SciTePress},
organization={INSTICC},
doi={10.5220/0011249500003443},
isbn={978-989-758-595-1},
}

in EndNote Style

TY - CONF

JO - Proceedings of the 4th International Conference on Biomedical Engineering and Bioinformatics - Volume 1: ICBEB,
TI - Synthesis Proposal of Immunosuppressive 9,10-secosteroid A from the Gorgonian Verrucella Umbraculum
SN - 978-989-758-595-1
AU - Yuan Z.
AU - Li H.
AU - Han Y.
PY - 2022
SP - 612
EP - 619
DO - 10.5220/0011249500003443