Total synthesis of sanglifehrin A

K. C. Nicolaou; Jinyou Xu; Fiona Murphy; Sofia Barluenga; Olivier Baudoin; Heng Xu Wei; David L.F. Gray; Takashi Ohshima

doi:10.1002/(SICI)1521-3773(19990816)38:16<2447::AID-ANIE2447>3.0.CO;2-O

Total synthesis of sanglifehrin A

K. C. Nicolaou, Jinyou Xu, Fiona Murphy, Sofia Barluenga, Olivier Baudoin, Heng Xu Wei, David L.F. Gray, Takashi Ohshima

Research output: Contribution to journal › Article › peer-review

61 Citations (Scopus)

Abstract

The immunosuppressive agent sanglifehrin A has been prepared for the first time by total synthesis. The construction of the macrocyclic unit of the target molecule was achieved through a selective intramolecular Stille coupling, and the spirolactam unit by Paterson-aldol reactions. The final steps involve an intermolecular Stille coupling and the opening of the internal acetal unit. This convergent synthesis opens the way for the synthesis of libraries of novel sanglifehrin analogues for biological screening.

Original language	English
Pages (from-to)	2447-2451
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	38
Issue number	16
DOIs	https://doi.org/10.1002/(SICI)1521-3773(19990816)38:16<2447::AID-ANIE2447>3.0.CO;2-O
Publication status	Published - Aug 12 1999
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)

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10.1002/(SICI)1521-3773(19990816)38:16<2447::AID-ANIE2447>3.0.CO;2-O

Cite this

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T1 - Total synthesis of sanglifehrin A

AU - Nicolaou, K. C.

AU - Xu, Jinyou

AU - Murphy, Fiona

AU - Barluenga, Sofia

AU - Baudoin, Olivier

AU - Wei, Heng Xu

AU - Gray, David L.F.

AU - Ohshima, Takashi

PY - 1999/8/12

Y1 - 1999/8/12

N2 - The immunosuppressive agent sanglifehrin A has been prepared for the first time by total synthesis. The construction of the macrocyclic unit of the target molecule was achieved through a selective intramolecular Stille coupling, and the spirolactam unit by Paterson-aldol reactions. The final steps involve an intermolecular Stille coupling and the opening of the internal acetal unit. This convergent synthesis opens the way for the synthesis of libraries of novel sanglifehrin analogues for biological screening.

AB - The immunosuppressive agent sanglifehrin A has been prepared for the first time by total synthesis. The construction of the macrocyclic unit of the target molecule was achieved through a selective intramolecular Stille coupling, and the spirolactam unit by Paterson-aldol reactions. The final steps involve an intermolecular Stille coupling and the opening of the internal acetal unit. This convergent synthesis opens the way for the synthesis of libraries of novel sanglifehrin analogues for biological screening.

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M3 - Article

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IS - 16

ER -

Total synthesis of sanglifehrin A

Abstract

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