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Total Synthesis of the Tetracyclic Sesquiterpene (±)‐Punctaporonin C
Author(s) -
Fleck Martin,
Bach Thorsten
Publication year - 2008
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.200801534
Subject(s) - intramolecular force , regioselectivity , epoxide , yield (engineering) , sesquiterpene , total synthesis , chemistry , carbon skeleton , stereochemistry , double bond , skeleton (computer programming) , natural product , wacker process , ring (chemistry) , organic chemistry , materials science , biology , catalysis , palladium , metallurgy , anatomy
Tailor made for the target molecule 2 , the carbon skeleton of the epoxide 1 was integrated entirely into the natural product. A regioselective intramolecular [2+2] photocycloaddition and subsequent Wacker oxidation enabled the specific and successive incorporation of the two terminal double bonds of 1 into the unusual oxatetracyclo[6.3.2.0 1,4 .0 5,13 ]tridecane skeleton of 2 , which was synthesized in 24 steps and 2.0 % overall yield. TBDMS= tert ‐butyldimethylsilyl.
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