Synthesis Toward and Stereochemical Assignment of Clathsterol: Exploring Diverse Strategies to Polyoxygenated Sterols.
Herein we describe a synthesis of the trisulfate derivative of clathsterol (1), a marine sterol endowed with impressive structural features and moderate inhibitory activity against HIV-1 reverse transcriptase. By synthesizing two possible isomers of the side chain, the stereochemistry of 1 is assigned. In creating chiral side chains from steroidal lactone, our strategies, including an addition/reduction procedure to give C22R-OH, an epoxide-opening reaction, and a [3.3]-rearrangement to induce the generation of C24S-Et and C24R-Et respectively, are highly flexible and complementary to each other.
Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
Tao
T
Zhou
Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
Feng
F
Feng
Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
Yong
Y
Shi
Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
Wei-Sheng
WS
Tian