Synthesis of ent-Cleistanthane Diterpenoid Spruceanol: Construction of an Aromatic C Ring via Lewis Acid-Controlled Regioselective Diels–Alder Cycloaddition
- Resource Type
- Authors
- Wei Cai; Song Zhiqiang; Huang Sujie; Jiabin Li; Jiajia Wu; Xiaowen Xue; Zhengyuan Xin
- Source
- The Journal of Organic Chemistry. 85:6709-6718
- Subject
- Spruceanol
010405 organic chemistry
Stereochemistry
Andrographolide
Organic Chemistry
Regioselectivity
010402 general chemistry
Ring (chemistry)
01 natural sciences
Cycloaddition
Terpenoid
0104 chemical sciences
Adduct
chemistry.chemical_compound
chemistry
Lewis acids and bases
- Language
- ISSN
- 1520-6904
0022-3263
The first synthesis of ent-cleistanthane-type diterpenoid spruceanol with significant anticancer activity is described. A chiral pool approach was employed with a linear sequence of 13 steps beginning from readily available and inexpensive andrographolide. The approach features the construction of an aromatic ring with hydroxyl and methyl groups at C-12 and C-13 of the target compound, respectively, via Lewis acid-controlled regioselective Diels-Alder cycloaddition and the regioselective removal of the primary hydroxyl group of the Diels-Alder adduct.