Connecting C-19 Norditerpenoids to C-20 Diterpenes: Total Syntheses of 6-Hydroxy-5,6-dehydrosugiol, 6-Hydroxysugiol, and Taiwaniaquinone H, and Formal Synthesis of Dichroanone

Oxidation of the B-ring of abietane derivatives by Sharpless dihydroxylation gave the natural products 6-hydroxy-5,6-dehydrosugiol and 6-hydroxysugiol. Moreover, further oxidation gave a hydroxy dione derivative that provides a synthetic entry into the C-19 taiwaniaquinoid family of natural products. This route is based on biosynthetic considerations and involves a benzilic acid rearrangement followed by decarboxylation. On the basis of this approach, a total synthesis of (-)-taiwaniaquinone H and a formal synthesis of (-)-dichroanone have been achieved.


Published in:
Synthesis-Stuttgart, 2223-2232
Year:
2010
Keywords:
Laboratories:




 Record created 2011-12-16, last modified 2018-09-13


Rate this document:

Rate this document:
1
2
3
 
(Not yet reviewed)