Enantiospecific Synthesis of the 14-Memberes Diene Unit of methyl Sarcophytoate

Minoru Yasuda; Mitsuaki Ide; Yuka Matsumoto; Masaya Nakata

doi:10.1055/s-1997-967

Synlett 1997; 1997(8): 899-902
DOI: 10.1055/s-1997-967

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Enantiospecific Synthesis of the 14-Memberes Diene Unit of methyl Sarcophytoate

Minoru Yasuda, Mitsuaki Ide, Yuka Matsumoto, Masaya Nakata^*

^*Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223, Japan, Fax: +81-45-563-0446; E-mail: msynktxa@applc.keio.ac.jp

Abstract

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The enantiospecific synthesis of the 14-membered diene unit of methyl sarcophytoate has been achieved by using the Sharpless asymmetric epoxidation, the aldol reaction, the oxy-Michael addition, and the modified Ito-Kodama cyclization as the key steps. All the carbon skeleton was derived from geraniol only.

methyl sarcophytoate - Sharpless asymmetric epoxidation - aldol reaction - oxy-Michael addition - Ito-Kodama cyclization

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