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southern and the C11−C25 northern fragments of amphidi-
nolides C, C2, C3, and F have been accomplished. The two
fragments were prepared from a common intermediate by
capitalizing on the latent structural homology within the
macrocycle. The C1−C9 fragment synthesis involved a
diastereoselective TBAF-mediated intramolecular hetero-Mi-
chael cyclization. Also employed was Hartung’s modified
Mukaiyama alkenol cyclization to construct the trans-
tetrahydrofuran ring in the C11−C25 northern fragment.
Another key transformation that was applied to complete the
C11−C25 northern fragment was the use of a chelated
Mukaiyama aldol reaction.
́ ̀
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ASSOCIATED CONTENT
* Supporting Information
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Philipps, P.; Furstner, A. Chem. - Eur. J. 2015, 21, 2398.
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Detailed experimental procedures and full spectroscopic
data for all compounds (PDF)
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AUTHOR INFORMATION
■
(14) (a) Schuch, D.; Fries, P.; Donges, M.; Per
́
ez, B.; Hartung, J. J.
Am. Chem. Soc. 2009, 131, 12918. (b) Inoki, S.; Mukaiyama, T. Chem.
Lett. 1990, 19, 67. (c) Menendez Perez, B.; Schuch, D.; Hartung, J.
̈
Corresponding Author
ORCID
́
́
Org. Biomol. Chem. 2008, 6, 3532. (d) Li, Y.; Zhou, F.; Forsyth, C. J.
Angew. Chem., Int. Ed. 2007, 46, 279.
Present Address
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Kenton, N.; Forsyth, C. J. Org. Lett. 2016, 18, 1824.
†(D.W.) Xiamen Intellectual Property Office, Room 1301
(West Building), 191 Changqing Rd, Xiamen, Fujian 36102, P.
R. China.
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
This work was supported by the Ohio State University, the
NIH funded OSU Chemistry & Biology Interface Program
(DA), and the Forsyth Research Fund.
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