Synthesis of the ABC ring system of Azaspiracid. 2. A systematic study into the effect of C(16) and C(17) substitution on bis-spirocyclization.
[reaction: see text] A systematic study into the effect of C(16) and C(17) substitution on the stereochemical outcome of bis-spirocyclization to form the ABC ring system of azaspiracid is disclosed. Successful construction of the natural 10R,13R bis-spirocyclic stereochemistry has been accomplished on the C(16) benzyloxy-containing precursor.
Carter
Rich G
RG
Department of Chemistry and Biochemistry, University of Mississippi, University, Mississippi 38677, USA. rich.carter@oregonstate.edu
Graves
David E
DE
Gronemeyer
Melissa A
MA
Tschumper
Gregory S
GS
D000478:Alkylation; D000818:Animals; D049872:Bivalvia / Q000737:chemistry; D008387:Marine Toxins / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D000095702:Polyether Toxins
D008387:Marine Toxins; D013141:Spiro Compounds; C406592:azaspiracid; D000095702:Polyether Toxins