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Sharpless Epoxidation

Sharpless Epoxidation

The conversion of allylic alcohols into epoxides using the chiral catalyst was discovered by K. Barry Sharpless and is known as Sharpless epoxidation. The use of a chiral catalyst enables the formation of one enantiomer of the product in excess. This chiral catalyst is mainly a chiral complex of titanium tetraisopropoxide and tartrate ester (specific stereoisomer). The stereoisomer used in the chiral catalyst dictates the formation of the enantiomer of the product. In other words, the use of...

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Related Experiment Video

Updated: Apr 30, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine

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Published on: February 16, 2018

Total synthesis of (-)-lepistine.

Yusuke Kitabayashi¹, Satoshi Yokoshima, Tohru Fukuyama

¹Graduate School of Pharmaceutical Sciences, Nagoya University, Furo-cho , Chikusa-ku, Nagoya 464-8601, Japan.

Organic Letters

|May 13, 2014

Summary

The first total synthesis of the natural product (-)-lepistine was achieved in 11 steps. Key steps included forming a 10-membered ring and constructing the aminal moiety.

Area of Science:

Organic Chemistry
Natural Product Synthesis

Background:

(-)-Lepistine is a natural product with a unique molecular structure.
The total synthesis of complex natural products is crucial for chemical research.

Purpose of the Study:

To achieve the first total synthesis of (-)-lepistine.
To develop an efficient synthetic route for (-)-lepistine.

Main Methods:

The synthesis commenced from (S)-glycidol.
A 10-membered ring was constructed through intramolecular epoxide opening using nosylamide.
Regioselective dehydration yielded an enol ether intermediate.
Aminal moiety construction was induced by nosyl group cleavage.

Main Results:

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The first total synthesis of (-)-lepistine was successfully completed in 11 steps.

The synthetic route established the feasibility of constructing the core structure of (-)-lepistine.

Conclusions:

The developed synthetic strategy provides a viable pathway for accessing (-)-lepistine.
This synthesis contributes to the field of natural product synthesis and methodology development.