Revolutionary research on the total synthesis of the antitumor macrolide natural product (-)-exiguolide achieved in only 13 steps.
Prof. Haruhiko Fuwa in Chuo University is leading Laboratory of Natural Products Chemistry investigating the structure, synthesis, and function of marine natural products that are potentially relevant to the discovery of new chemotherapeutic agents.
Mr. Daichi Mizukami, a master's course student, Graduate School of Science and Engineering (completed in March 2022), and Professor Haruhiko Fuwa, Faculty of Science and Engineering, have published a revolutionary research paper. In this paper, it is reported that the synthesis of macrolides which previously required more than 20 multi-step reactions, can be made more efficiently by using our originally developed catalytic sequential reaction, and that the total synthesis of the antitumor macrolide natural product (-)-exiguolide was actually achieved in only 13 steps.
The synthetic method reported in this paper is highly versatile and is expected to streamline the synthesis of various macrolide compounds in the future.
The paper is published in Angewandte Chemie International Edition and selected as frontispiece article.
It has also been highlighted in Synfacts as a notable paper.
Paper Published in Angewandte Chemie International Edition 2022, 61, e202202549.
Author: D. Mizukami, K. Iio, M. Oda, Y. Onodera, H. Fuwa*
Title: Tandem Macrolactone Synthesis: Total Synthesis of (−)-Exiguolide by a Macrocyclization/Transannular Pyran Cyclization Strategy