A concise total synthesis of DL-histrionicotoxin.
The synthesis of (+/-)-histrionicotoxin has been achieved in just nine steps using a two-directional synthesis strategy. Key reactions include a two-directional cross-metathesis, a tandem oxime formation/Michael addition/1,4-prototopic shift/[3 + 2]-cycloaddition cascade, a selective Z,Z-bisenyne formation, and a one-pot N-O and bischloroacetylene reduction.
Karatholuvhu
Maheswaran S
MS
School of Chemical Sciences and Pharmacy, University of East Anglia, Norwich NR4 7TJ, United Kingdom.
Sinclair
Alex
A
Newton
Annabella F
AF
Alcaraz
Marie-Lyne
ML
Stockman
Robert A
RA
Fuchs
Philip L
PL
D000480:Alkynes / Q000737:chemistry; D000664:Amphibian Venoms / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D001001:Anura; D013237:Stereoisomerism
D000480:Alkynes; D000664:Amphibian Venoms; C007948:histrionicotoxin