A spirodiepoxide-based strategy to the A-B ring system of pectenotoxin 4.
[reaction: see text] A synthesis of a pectenotoxin 4 C1-C15 segment is reported. Suitable C1-C7 and C8-C15 segments were prepared, coupled, converted to I and the C3-hydroxy variant, and then cyclized. Key findings include the stereoselective conversion of the allene to the corresponding spirodiepoxide, oxidative cleavage of the p-methoxybenzyl ether, and cyclization of the spirodiepoxide to spiroketal II.
Lotesta
Stephen D
SD
Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854, USA.
Hou
Yongquan
Y
Williams
Lawrence J
LJ
D000466:Alkadienes / Q000737:chemistry; D003500:Cyclization; D004852:Epoxy Compounds / Q000737:chemistry*; D018942:Macrolides / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D000095702:Polyether Toxins
D000466:Alkadienes; D004852:Epoxy Compounds; D018942:Macrolides; C471226:pectenotoxin-4; D000095702:Polyether Toxins; C025947:propadiene