TY - JOUR
T1 - Total Syntheses of (+)-Aquatolide and Related Humulanolides
AU - Takao, Ken ichi
AU - Kai, Hirotaka
AU - Yamada, Ai
AU - Fukushima, Yuuki
AU - Komatsu, Daisuke
AU - Ogura, Akihiro
AU - Yoshida, Keisuke
PY - 2019/7/15
Y1 - 2019/7/15
N2 - The short, efficient total synthesis of (+)-aquatolide was achieved by a biomimetic transannular [2+2] photocycloaddition, and provides the first example of constructing a 5/5/4/8-ring system from asteriscunolides. Furthermore, the reaction leading to a 5/4/4/7-ring system, the originally proposed structure of aquatolide, was also developed. This strategy achieved syntheses of five more humulanolides, (−)-asteriscunolides A, C, D, and I, and (+)-tetradehydroasteriscanolide.
AB - The short, efficient total synthesis of (+)-aquatolide was achieved by a biomimetic transannular [2+2] photocycloaddition, and provides the first example of constructing a 5/5/4/8-ring system from asteriscunolides. Furthermore, the reaction leading to a 5/4/4/7-ring system, the originally proposed structure of aquatolide, was also developed. This strategy achieved syntheses of five more humulanolides, (−)-asteriscunolides A, C, D, and I, and (+)-tetradehydroasteriscanolide.
KW - biomimetic synthesis
KW - cycloaddition
KW - metathesis
KW - terpenoids
KW - total synthesis
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U2 - 10.1002/anie.201904404
DO - 10.1002/anie.201904404
M3 - Article
C2 - 31115973
AN - SCOPUS:85068154162
VL - 58
SP - 9851
EP - 9855
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
SN - 1433-7851
IS - 29
ER -