Diphenanthro[4,3-d:3',4'-f][1,3,2]dioxaphosphepin,18-hydroxy-8,9-diphenyl-, 18-oxide, (8aS)-

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CAS: 871130-17-5
MF: C40H25O4P
MW: 600.5979
Synonyms: Diphenanthro[4,3-d:3',4'-f][1,3,2]dioxaphosphepin,18-hydroxy-8,9-diphenyl-, 18-oxide, (8aS)-

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Pavel Nagorny

University of Michigan
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Gareth Morris

The University of Manchester
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Simon J. Webb

University of Manchester
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Kazuhiro Higuchi

Meiji Pharmaceutical University
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Co-reporter: Kazuhiro Higuchi, Shin Suzuki, Reeko Ueda, Norifumi Oshima, Emiko Kobayashi, Masanori Tayu, and Tomomi Kawasaki
pp: 154-157
Publication Date(Web):December 19, 2014
DOI: 10.1021/ol5033865
The asymmetric total synthesis of (−)-leuconoxine has been achieved. The desymmetrization of a prochiral diester using a chiral phosphoric acid catalyst produced a highly enantioenriched lactam with excellent yield. The ring construction featuring an intramolecular N-acyliminium cyclization and the one-step pyrrolidone formation using Bestmann’s ylide was successfully accomplished.

Tomomi Kawasaki

Meiji Pharmaceutical University
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Co-reporter: Kazuhiro Higuchi, Shin Suzuki, Reeko Ueda, Norifumi Oshima, Emiko Kobayashi, Masanori Tayu, and Tomomi Kawasaki
pp: 154-157
Publication Date(Web):December 19, 2014
DOI: 10.1021/ol5033865
The asymmetric total synthesis of (−)-leuconoxine has been achieved. The desymmetrization of a prochiral diester using a chiral phosphoric acid catalyst produced a highly enantioenriched lactam with excellent yield. The ring construction featuring an intramolecular N-acyliminium cyclization and the one-step pyrrolidone formation using Bestmann’s ylide was successfully accomplished.

Jonathan Clayden

University of Manchester
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