Synthetic Study on Macrocyclic Musks, Mints, and Jasmine Perfumes

Chapter 25

Downloaded by OHIO STATE UNIV LIBRARIES on September 7, 2012 | http://pubs.acs.org Publication Date: November 23, 2004 | doi: 10.1021/bk-2005-0892.ch025

Synthetic Study on Macrocyclic Musks, Mints, and Jasmine Perfumes Utilizing Ti-Claisen and Aldol Reactions Yoo Tanabe Department of Chemistry, School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo 669-1337, Japan

We developed powerful Ti- or Zr-Claisen condensation between esters and direct crossed Ti-aldol addition between ketones and ketones or aldehydes. These reactions were successfully applied to the short and practical method for synthesizing some natural macrocyclic musks (civetone and muscone), mints (mintlactone and menthofuran), and a jasmine perfume.

We have been engaged in the exploitation of new original and practical organic reactions directed toward the process chemistry and its application to the syntheses of useful fine chemicals and structurally interesting natural products. Especially, we focused our attention on the Ti (or Zr)-Claisen condensations * and related direct aldol additions from a recent standpoint of the environmentally benign (green) organic synthesis. 1

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