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Total Synthesis of (−)‐Dolastatrienol
Author(s) -
Leung Lai To,
Chiu Pauline
Publication year - 2015
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201403325
Subject(s) - intramolecular force , total synthesis , tricyclic , natural product , chemistry , rhodium , heck reaction , cycloaddition , stereochemistry , cascade reaction , combinatorial chemistry , organic chemistry , catalysis , palladium
The first asymmetric total synthesis of the tricyclic diterpenoid natural product (−)‐dolastatrienol has been accomplished using a rhodium(II)‐catalyzed carbene cyclization cycloaddition cascade reaction as the key step to construct the [5.4.0]carbobicyclic core. An intramolecular Heck reaction furnished the tricyclic skeleton and a challenging methylenation completed the synthesis of the target.