Toward an enantioselective total synthesis of sarain A: construction of an advanced intermediate and rearrangement of the sarain A core under mild conditions.
A high-yielding N-sulfonyliminium ion-enoxysilane cyclization and a ring-closing metathesis are key steps in the enantioselective synthesis of late-stage intermediates en route to sarain A. Also revealed is an unprecedented rearrangement of the tetracyclic sarain A core under mildly acidic conditions. [structure: see text]
Douglas
Christopher J
CJ
Department of Chemistry, University of California-Irvine, 516 Rowland Hall, Irvine, CA 92697-2025, USA.
Hiebert
Sheldon
S
Overman
Larry E
LE
D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D007202:Indicators and Reagents; D015394:Molecular Structure; D013237:Stereoisomerism
D001952:Bridged-Ring Compounds; D007202:Indicators and Reagents; C410431:sarain A