Crotepoxide synthesis

Microbially produced (2.S .3.S )-// .v-dihvdroxy-2.3-dihvdrobenzoic acid was used in the synthesis of enf-streptol, enf-senepoxide, and /so-crotepoxide (Fig. 33). The short and efficient synthesis of these biologically active compounds included the esterification of the carboxylic acid and protection of the diol moiety, delivering control of the regio- and stereoselectivity of the following epoxidation or dihydrox-ylation steps [178, 180]. 

Lorbach V, Franke D et al (2002) Cyclohexadiene-trams-diols as versatile starting material in natural product synthesis short and efficient synthesis of wo-crotepoxide and ent-senepox-ide. Chem Commun 38 494-495... 

The enantiospecific synthesis of naturally occurring cyclohexane epoxides such as (+)-crotepoxide and (+)-boesenoxide was accomplished by T.K.M. Shing et al. The key Intermediate 1,3-cyclohexadlene was prepared using the Corey-Winter protocol on a c/s-vicinal diol. The resulting diene was then converted to the natural product after several steps. 

Photooxygenation of a -dimethylstyrene. This reaction has been used in a synthesis of ( )-crotepoxide (6), a natural epoxide with activity against some... 

The antitumour agent crotepoxide (165), also known as futoxide, has been synthesized from the e do-peroxide intermediates (163) and (164), which were obtained from the addition of singlet oxygen to the diene (162) (Scheme 47)." A closely related synthesis, involving addition of singlet oxygen to a styrene derivative, has also been reported. ... 

Matsumoto, M., Dobashi, S., and Kondo, K., Sensitized photooxygenation of 6,6-dimethylstyrenes synthesis of ( )-crotepoxide. Tetrahedron Lett., 3361,1977. 

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