
Tetrahedron p. 8481 - 8493 (2001)
Update date:2022-07-30
Topics:
Sy, Lai-King
Cheung, Kung-Kai
Zhu, Nian-Yong
Brown, Geoffrey D
The novel cadinane diol, arteannuin O (1), has been obtained from Artemisia annua and its structure has been established by 2D NMR and X-ray crystallography. A reconstructive synthesis of arteannuin O from artemisinin is described, which also yields the natural products arteannuin K and arteannuin L. Mechanistic considerations have led to the conclusion that the stereochemistry of the 5-hydroxyl group was wrongly assigned when arteannuins K, L and M were first reported as natural products. This was confirmed by derivatization of synthetic arteannuins K, L and M as their Mosher esters.
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