Synthesis of plagiochiline N from santonin.
This article reports the transformation of O-acetylisophotosantonin, obtained by photochemical rearrangement of santonin, into plagiochiline N, an ent-2,3-secoaromadendrane isolated from Plagiochila ovalifolia. The synthesis was carried out in a sequence involving as the key steps (a) the substitution of the lactone moiety by a gem-dimethylcyclopropane ring through a synthetic intermediate having a C(6)-C(7) double bond and (b) the ozonolysis of the C(2)-C(3) bond followed by cyclization to the dihydropyran ring characteristic of plagiochiline N. Spectroscopic data of the synthetic product fully coincided with the reported data for the natural product.
Blay
G
G
Departament de Química Orgànica, Facultat de Química, Universitat de València, E-46100 Burjassot, València, Spain.
Cardona
L
L
García
B
B
Lahoz
L
L
Pedro
J R
JR
D000475:Alkenes / Q000138:chemical synthesis* / Q000302:isolation & purification* / Q000494:pharmacology; D000969:Antinematodal Agents / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry; D012500:Santonin / Q000737:chemistry*; D013861:Thiocyanates / Q000138:chemical synthesis* / Q000302:isolation & purification* / Q000494:pharmacology
D000475:Alkenes; D000969:Antinematodal Agents; D013861:Thiocyanates; C444280:thiocyanatin A; C444279:thiocyanatin B; D012500:Santonin