Dr. Jian Hao’s Group Total Synthesis of Drospirenone Derivatives The total synthesis of 6β,7β,16β,17β-dimethylene-3-one-14β-Androsta-4-en[17(β-1’)-spiro-5’]perhydrofuran-2’-one 4, which is known as key derivative of drospirenone, has been achieved recently in lab scale through the 8-step process starting from the commercially available dehydroepiandrosterone. The key intermediates 2 and 3 which contain the cyclopropanyl moieties have been identified by X-ray diffraction. The optimization of reaction conditions is currently under investigation. O

H HO

1

O

H HO

2

O

O O H O

H O

3

4

Patents Applied: CN200610026942.2, CN200610026944.1

Chunfang Zheng was born in Guangdong Province. Shangqing Yao was born in Luan, Anhui Province. She received her B.S.degree in Material Science and He received his B.S.degree in Applied Chemistry in Engineering in 2001 form Hunan University. She is 2005 form Anhui Normal University. He is now a now a senior postgraduate student in department of postgraduate student in department of chemistry of chemistry of Shanghai University. Her research Shanghai University. His research interests include interests include the synthesis of Drospirenone and its the synthesis of Drospirenone and its derivatives. derivatives. For more information, please visit our group website: http://jhaocn.googlepages.com/

Dr. Jian Hao’s Group Grignard Cyclization Reaction of Fluorinated N-aryl Imidoyl Chlorides. A Novel and Facile Access to 2Fluoroalkylindoles 2-Fluoroalkyl substituted indole derivatives were simply prepared via the Grignard cyclization reaction (GCR) of corresponding fluorinated N-aryl imidoyl chlorides in good yields. This approach provides a novel and facile access to the biologically important 2fluoroalkylindole derivatives. R1 R2

R1

RFCO2H

R1

NH2 PPh3, TEA CCl4 83-97% RF = CF3, CF2H, n-C3F7 R1 = H, R2 = H, 4-OCH3, 4-NO2, 5-F, 5-Cl, 3-Cl, 4-Cl or R1 = CH3, R2 = H OH NH2

Br

NBS R2 Cl 56-92%

R2

N

RF

1

Cl N 2

N H OH 88%

N

Cl

ps st e 58 %

o tw Br

6

89%

CF3

% 75

4a

%

4

N 3

Synthetic Applications:

N PG

61

CF3

3a

NBS

RF

Mg

Cl

Cl

CCl4, TFA

hv

Mg -87 %

R1

PPh3, TEA

CF3

50

R2

CF3

N H

RF

COOH N H

CF3

7 CH(CO2CH3)2 N CF3 PG 8 (PG=4-Cl-PhCO-) COOEt COOEt NHAc CF3 N PG 9 (PG=PhSO2-)

Fenglian Ge was born in Shandong Province. She received her B.S.degree in College of Chemistry ,Chemical Engineering and Material Science ,Shandong Normal University in 2004 . She is now a senior postgraduate student in department of chemistry of Shanghai University. Her research interests include the development of new methodologies for the synthesis of novel fluorinecontaining heterocycles. She is currently holding more than 10 patents.

Zengxue Wang was born in Shandong Province. He received his B.S.degree in College of Chemistry and Chemical Engineering of Linyi Normal University in 2005. He is now a postgraduate student in department of chemistry of Shanghai University. His research interests include the development of new methodologies for the synthesis of novel fluorinecontaining heterocycles.

For more information, please visit our group website: http://jhaocn.googlepages.com/