Remote stereocontrol in [3,3]-sigmatropic rearrangements: Application to the total synthesis of the immunosuppressant mycestericin G

Nathan W G Fairhurst, Mary F Mahon, R H Munday, David R Carbery

Research output: Contribution to journalArticle

23 Citations (Scopus)
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Abstract

The Ireland - Claisen [3,3]-sigmatropic rearrangement has been used to access biologically important β,β′-dihydroxy α-amino acids. The rearrangement reported is highly stereoselective and offers excellent levels of remote stereocontrol. This strategy has been used to synthesize the natural immunosuppressant mycestericin G and ent-mycestericin G, allowing for a revision of absolute configuration of this natural product.
Original languageEnglish
Pages (from-to)756-759
Number of pages4
JournalOrganic Letters
Volume14
Issue number3
Early online date12 Jan 2012
DOIs
Publication statusPublished - 3 Feb 2012

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Ireland
Immunosuppressive Agents
amino acids
synthesis
products
configurations
Biological Products
Amino Acids
mycestericin F

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Remote stereocontrol in [3,3]-sigmatropic rearrangements: Application to the total synthesis of the immunosuppressant mycestericin G. / Fairhurst, Nathan W G; Mahon, Mary F; Munday, R H; Carbery, David R.

In: Organic Letters, Vol. 14, No. 3, 03.02.2012, p. 756-759.

Research output: Contribution to journalArticle

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