PubAg

Main content area

Synthesis of the cyclohexene segment of portimine

Author:
Saito, Takafumi, Fujiwara, Kenshu, Kondo, Yoshihiko, Akiba, Uichi, Suzuki, Takanori
Source:
Tetrahedron letters 2019 v.60 no.4 pp. 386-389
ISSN:
0040-4039
Subject:
Miozoa, acylation, cyclohexenes, cytotoxins, diastereoselectivity, dihydroxylation, moieties
Abstract:
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.
Agid:
6290019