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Synthesis of the cyclohexene segment of portimine
- Saito, Takafumi, Fujiwara, Kenshu, Kondo, Yoshihiko, Akiba, Uichi, Suzuki, Takanori
- Tetrahedron letters 2019 v.60 no.4 pp. 386-389
- Miozoa, acylation, cyclohexenes, cytotoxins, diastereoselectivity, dihydroxylation, moieties
- The synthesis of the cyclohexene segment of portimine, a marine cytotoxin from the dinoflagellate Vulcanodinium rugosum, was achieved. The route includes an acylation/aldol reaction from 3-ethoxycyclohex-2-enone to create the C3 center, the 1,4-addition of a vinyl group at C16, the diastereoselective dihydroxylation of the vinyl group to generate the C15 center, a vinylation/dehydration sequence to set up the diene moiety, and stepwise installation of the amino-group-substituted C1 unit.