Amphidinolide B: asymmetric synthesis of a C7-C20 synthon.
[reaction: see text] An asymmetric synthesis of a C(7)-C(20) synthon of amphidinolide B is described. The synthesis entails the construction of C(7)-C(13) and C(14)-C(20) fragments and makes extensive use of catalytic asymmetric bond constructions to establish the requisite stereochemical relationships. Fragment coupling proceeds by Suzuki cross-coupling and installs the trisubstituted diene unit that is among amphidinolide B's defining structural features.
Gopalarathnam
Apsara
A
Department of Chemistry, University of Pittsburgh, Pennsylvania 15260, USA.
Nelson
Scott G
SG
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D000097442:Amphidinolides
D019086:Bridged Bicyclo Compounds, Heterocyclic; C062197:amphidinolide D; D000097442:Amphidinolides