A Proposal for the Synthesis Route of Lyaline

Shuang Wu, Xu Han, Jiedong Li

2022

Abstract

Lyaline is a monoterpene indole alkaloid first isolated in 1974. After attempts of proposing a synthesis route of this compound, researchers found its structure to be unstable and that the proposed structure to be incorrect. Later researchers revised the structure and set lyaline as the first naturally occurring nacycline analogue. While most previous research examine the spectroscopic data of lyaline and came up with a structure, this work assess the possibility of retrosynthesizing this compound and propose a theoretical synthesis pathway for the revised structure of lyaline. Through online research and books, we decided to retrosynthesize this molecule by first separating it into a cyclohexene and an indole. And with 3 starting materials—molecule 1 and 2 presented below, and an indole—it is possible to synthesis lyaline through a series of nucleophilic substitutions and Dials-Alder cyclic addition. This proposal will finally make the molecule of lyaline, though not completed. The following researches can be done by experimenting and resolving the stereoselectivity of the specific Dials-Alder reaction and using a better protection to increase the yield of the amine formation.

Paper Citation

in Harvard Style

Wu S., Han X. and Li J. (2022). A Proposal for the Synthesis Route of Lyaline. In Proceedings of the 1st International Conference on Food Science and Biotechnology - Volume 1: FSB; ISBN 978-989-758-638-5, SciTePress, pages 134-137. DOI: 10.5220/0012003600003625

in Bibtex Style

@conference{fsb22,
author={Shuang Wu and Xu Han and Jiedong Li},
title={A Proposal for the Synthesis Route of Lyaline},
booktitle={Proceedings of the 1st International Conference on Food Science and Biotechnology - Volume 1: FSB},
year={2022},
pages={134-137},
publisher={SciTePress},
organization={INSTICC},
doi={10.5220/0012003600003625},
isbn={978-989-758-638-5},
}

in EndNote Style

TY - CONF

JO - Proceedings of the 1st International Conference on Food Science and Biotechnology - Volume 1: FSB
TI - A Proposal for the Synthesis Route of Lyaline
SN - 978-989-758-638-5
AU - Wu S.
AU - Han X.
AU - Li J.
PY - 2022
SP - 134
EP - 137
DO - 10.5220/0012003600003625
PB - SciTePress