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Total Synthesis of (±)‐Phomoidride D.

Authors :
Leung, Joyce C.
Bedermann, Aaron A.
Njardarson, Jón T.
Spiegel, David A.
Murphy, Graham K.
Hama, Naoto
Twenter, Barry M.
Dong, Ping
Shirahata, Tatsuya
McDonald, Ivar M.
Inoue, Munenori
Taniguchi, Nobuaki
McMahon, Travis C.
Schneider, Christopher M.
Tao, Nancy
Stoltz, Brian M.
Wood, John L.
Source :
Angewandte Chemie International Edition; 2/12/2018, Vol. 57 Issue 7, p1991-1994, 4p
Publication Year :
2018

Abstract

Abstract: Described herein is a synthetic strategy for the total synthesis of (±)‐phomoidride D. This highly efficient and stereoselective approach provides rapid assembly of the carbocyclic core by way of a tandem phenolic oxidation/intramolecular Diels–Alder cycloaddition. A subsequent SmI<subscript>2</subscript>‐mediated cyclization cascade delivers an isotwistane intermediate poised for a Wharton fragmentation that unveils the requisite bicyclo[4.3.1]decene skeleton and sets the stage for synthesis completion. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
14337851
Volume :
57
Issue :
7
Database :
Complementary Index
Journal :
Angewandte Chemie International Edition
Publication Type :
Academic Journal
Accession number :
127846903
Full Text :
https://doi.org/10.1002/anie.201712369