Stereospecific Total Synthesis of the Antiviral Agent Hamigeran B—Use of Large Silyl Groups to Enforce Facial Selectivity and to Suppress Hydrogenolysis | Zendy

Clive Derrick L. J. | Zendy; Wang Jian | Zendy

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Stereospecific Total Synthesis of the Antiviral Agent Hamigeran B—Use of Large Silyl Groups to Enforce Facial Selectivity and to Suppress Hydrogenolysis

Author(s) -

Clive Derrick L. J.,

Wang Jian

Publication year - 2003

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.200351519

Subject(s) - selectivity , stereoselectivity , chemistry , hydrogenolysis , enone , stereospecificity , natural product , silylation , stereochemistry , total synthesis , double bond , organic chemistry , catalysis

Stereoselective hydrogenation of the tetrasubstituted double bond in enone 1 is possible, provided the keto group at C7 is first removed and the α face is blocked by tert ‐butyldimethylsiloxy groups at positions 10 and 11. The resulting product 2 is easily converted into hamigeran B ( 3 ), a marine natural product with powerful activity against herpes and polio viruses. Si*= t BuMe 2 Si.

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