Total synthesis of norzoanthamine.
Norzoanthamine, an alkaloid isolated from Zoanthus sp., can suppress the loss of bone weight and strength in ovariectomized mice. Norzoanthamine derivatives can also strongly inhibit the growth of P-388 murine leukemia cell lines and human platelet aggregation. However, norzoanthamine's densely functionalized complex stereostructure and scarce availability from natural sources have proved a synthetic challenge. We report the stereoselective total synthesis of norzoanthamine in 41 steps, with an overall yield of 3.5% (an average of 92% yield each step).
Miyashita
Masaaki
M
Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan. miyasita@sci.hokudai.ac.jp
Sasaki
Minoru
M
Hattori
Izumi
I
Sakai
Mio
M
Tanino
Keiji
K
D000470:Alkaloids; D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006576:Heterocyclic Compounds, 4 or More Rings; D008968:Molecular Conformation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
D000470:Alkaloids; D001381:Azepines; D006576:Heterocyclic Compounds, 4 or More Rings; D011804:Quinolines; C400280:norzoanthamine