Publication Date

2020

First Advisor

Kevin M. Shea

Document Type

Honors Project

Degree Name

Bachelor of Arts

Department

Chemistry

Keywords

Diels-Alder reaction, Pauson-Khand reaction, Steroid synthesis, Organic synthesis, Cobalt-complexed alkyne, One-pot synthesis

Abstract

Steroids are a class of polycyclic compounds that have diverse biological functions. Some are components of cell membranes such as cholesterol, and others are important building blocks for hormones. We aim to develop a tandem intramolecular Diels- Alder/Pauson-Khand reaction to generate a tetracyclic steroid core 1 from a single acyclic molecule 2. In this new reaction strategy, dicobalt octacarbonyl, when complexed to the acyclic alkynyl precursor, is proposed to both activate the diene for the Diels-Alder reaction and participate in the successive Pauson-Khand reaction (Scheme 1).

Initial studies have shown that synthesizing the acyclic tetraenyne 2 is especially challenging. The current synthesis of tetraenyne 2 involves two C-C bond forming steps. The first C-C bond formation is a Suzuki coupling that yields a conjugated dienynyl alcohol, which undergoes subsequent oxidation to the corresponding aldehyde. The second C-C bond forming step is currently under development. An aldol condensation of the prepared aldehyde is proposed to yield the desired tetraenyne 2.

Rights

©2020 Eve Yuanwei Xu. Access limited to the Smith College community and other researchers while on campus. Smith College community members also may access from off-campus using a Smith College log-in. Other off-campus researchers may request a copy through Interlibrary Loan for personal use.

Language

English

Comments

91 pages : illustrations. Includes bibliographical references (pages 87-91)

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