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Total Syntheses of Cochliomycin B and Zeaenol
Author(s) -
Gao Yangguang,
Liu Jun,
Wang Linlin,
Xiao Ming,
Du Yuguo
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301613
Subject(s) - chemistry , stereocenter , stereochemistry , metathesis , total synthesis , ring closing metathesis , transesterification , combinatorial chemistry , enantioselective synthesis , organic chemistry , catalysis , polymer , polymerization
Divergent syntheses of two 14‐membered resorcylic acid lactones (RALs), cochliomycin B ( 6 ) and zeaenol ( 22 ), have been accomplished. The key feature in our strategy was the facile construction of three contiguous stereogenic centers in the title molecules by using natural L ‐arabinose as the chiral template. The key reactions included Takai olefination, Suzuki cross coupling, transesterification, and a late‐stage ring‐closing metathesis (RCM).