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Synthesis of 3‐Oxaterpenoids and Its Application in the Total Synthesis of (±)‐Moluccanic Acid Methyl Ester
Author(s) -
Li Bin,
Lai YinChang,
Zhao Yujun,
Wong YiuHang,
Shen ZhiLiang,
Loh TeckPeng
Publication year - 2012
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.201205981
Subject(s) - polyene , prins reaction , chemistry , total synthesis , alcohol , organic chemistry , intermolecular force , polyolefin , catalysis , molecule , layer (electronics)
Cascades : An InBr 3 ‐catalyzed intermolecular polyene cyclization initiated by a Prins reaction provides a concise approach to 3‐oxaterpenoid derivatives. The reaction is compatible with various aldehydes, ketones, and polyolefin–alcohol substrates. In addition, the total synthesis of (±)‐moluccanic acid methyl ester was achieved in seven steps by using such a Prins–polyene cyclization as the key step.