Toward the development of a general chiral auxiliary. A total synthesis of (+)-tetronolide via a tandem ketene-trapping [4 + 2] cycloaddition strategy.
A highly convergent, enantioselective total synthesis of the aglycone of the tetrocarcins, (+)-tetronolide, is described. The synthesis highlights the use of several new methods, including camphor auxiliary-directed asymmetric alkylation and the enantioselective preparation of acyclic mixed acetals bearing chirality at the acetal center, and the highly efficient connection of the two major precursors via a ketene-trapping/intramolecular [4 + 2] cycloaddition strategy.
Boeckman
Robert K
RK
Department of Chemistry, University of Rochester, P.O. Box 270216, Hutchison Hall, Rochester, New York 14627-0216, USA. rkb@rkbmac.chem.rochester.edu
Shao
Pengcheng
P
Wrobleski
Stephen T
ST
Boehmler
Debra J
DJ
Heintzelman
Geoffrey R
GR
Barbosa
Antonio J
AJ
D000617:Aminoglycosides / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D005030:Ethylenes / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000617:Aminoglycosides; D005030:Ethylenes; D007659:Ketones; C523037:tetronolide; C008223:ketene