Expedient construction of the Ziegler intermediate useful for the synthesis of forskolin via consecutive rearrangements.
The Ziegler intermediate, useful for the total synthesis of forskolin, was synthesized in 10 reaction steps starting from commercially available alpha-ionone. This highly efficient synthesis relies on the success of two consecutive highly regio- and stereoselective rearrangements. The current synthesis has not only established an efficient synthetic route to access the Ziegler intermediate but it has also paved a way to the structural optimization of forskolin.
Ye
Heping
H
Laboratory of Molecular Engineering and Laboratory of Natural Product Synthesis, Guangzhou Institute of Biomedicine and Health, The Chinese Academy of Sciences, Guangzhou 510663, China.
Deng
Gang
G
Liu
Jun
J
Qiu
Fayang G
FG
D031330:Coleus / Q000737:chemistry; D005576:Colforsin / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D045792:Norisoprenoids / Q000737:chemistry*; D013237:Stereoisomerism
D045792:Norisoprenoids; D005576:Colforsin; C011879:alpha-ionone