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The First Total Synthesis of Tricolorin A
Author(s) -
Lu ShouFu,
O'yang QinQin,
Guo ZhongWu,
Yu Biao,
Hui YongZheng
Publication year - 1997
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199723441
Subject(s) - total synthesis , tetrasaccharide , regioselectivity , yield (engineering) , sequence (biology) , stereochemistry , chemistry , organic chemistry , physics , biochemistry , polysaccharide , thermodynamics , catalysis
A regioselective macrolactonization and a one‐pot synthesis are the key steps in the first total synthesis of tricolorin A ( 1 ), the principal component of a plant used in traditional Mexican agriculture for weed control. The synthesis of this macrolactone tetrasaccharide, which starts from D ‐(+)‐mannitol, contains 45 steps with a longest linear sequence of 20 steps (overall yield 0.65%).