Stereoselective synthesis of methyl (11S,12S,13S)-(9Z,15Z)-11-hydroxy-12,13-epoxy octadecadienoate from D-mannose

DOI: 10.1016/S0040-4020(01)81295-3

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Tetrahedron p. 4665 - 4670 (1993)

Update date:2022-08-03

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Article abstract of DOI:10.1016/S0040-4020(01)81295-3

The title compound, a self defensive substance against the rice blast disease, was synthesized from D-mannose in ten steps. The key intermediate 6 was prepared with Grignard addition of lactol 5 in favoured anti-selectivity.

Full text of DOI:10.1016/S0040-4020(01)81295-3

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Product name:(Z)-10-{(4S,5S)-2,2-Dimethyl-5-[(Z)-(R)-1-(toluene-4-sulfonyloxy)-hex-3-enyl]-[1,3]dioxolan-4-yl}-dec-9-enoic acid ethyl ester

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