Total synthesis and stereochemical confirmation of manassantin A, B, and B1.
Stereocontrolled total syntheses of manassantins A, B, and B1 and saucerneol are described for the first time based on a novel cycloetherification of end-differentiated benzylic alcohols as a common intermediate. [structure: see text].
Hanessian
Stephen
S
Department of Chemistry, Université de Montréal, C.P. 6128, Succursale Centre-ville, Montréal, Québec H3C 3J7, Canada. stephen.hanessian@umontreal.ca
Reddy
Gone Jayapal
GJ
Chahal
Navjot
N
D014150:Antipsychotic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D001592:Benzyl Alcohols / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D051793:Hypoxia-Inducible Factor 1 / Q000037:antagonists & inhibitors; D007202:Indicators and Reagents; D017705:Lignans; D008745:Methylation; D009570:Nitriles / Q000737:chemistry; D032134:Saururaceae / Q000737:chemistry; D013237:Stereoisomerism; D014409:Tumor Necrosis Factor-alpha / Q000037:antagonists & inhibitors
D014150:Antipsychotic Agents; D001592:Benzyl Alcohols; D005663:Furans; D051793:Hypoxia-Inducible Factor 1; D007202:Indicators and Reagents; D017705:Lignans; D009570:Nitriles; D014409:Tumor Necrosis Factor-alpha; C430593:cyanohydrin; C482885:manassantin B; C054895:manassantin A