Concise, stereocontrolled synthesis of the citrinadin B core architecture

Carlos A. Guerrero; Erik J. Sorensen

doi:10.1021/ol2020362

Concise, stereocontrolled synthesis of the citrinadin B core architecture

Carlos A. Guerrero, Erik J. Sorensen

Chemistry

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

28 Scopus citations

Abstract

A concise, stereocontrolled synthesis of the citrinadin B core architecture from scalemic, readily available starting materials is disclosed. Highlights include ready access to both cyclic tryptophan tautomer and trans-2,6- disubstituted piperidine fragments, an efficient, stereoretentive mixed Claisen acylation for the coupling of these halves, and further diastereoselective carbonyl addition and oxidative rearrangement for assembly of the core.

Original language	English (US)
Pages (from-to)	5164-5167
Number of pages	4
Journal	Organic letters
Volume	13
Issue number	19
DOIs	https://doi.org/10.1021/ol2020362
State	Published - Oct 7 2011

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol2020362

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abstract = "A concise, stereocontrolled synthesis of the citrinadin B core architecture from scalemic, readily available starting materials is disclosed. Highlights include ready access to both cyclic tryptophan tautomer and trans-2,6- disubstituted piperidine fragments, an efficient, stereoretentive mixed Claisen acylation for the coupling of these halves, and further diastereoselective carbonyl addition and oxidative rearrangement for assembly of the core.",

author = "Guerrero, {Carlos A.} and Sorensen, {Erik J.}",

note = "Funding Information: The authors are grateful to Professor E. S. R. Gopal, Director, National Physical Laboratory, New Delhi for his keen interest in this work. Financial assistance from the Department of Biotechnology, Government of India, New Delhi under Grant No. BT/02/038/93-PID is gratefully acknowledged.",

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AU - Guerrero, Carlos A.

AU - Sorensen, Erik J.

N1 - Funding Information: The authors are grateful to Professor E. S. R. Gopal, Director, National Physical Laboratory, New Delhi for his keen interest in this work. Financial assistance from the Department of Biotechnology, Government of India, New Delhi under Grant No. BT/02/038/93-PID is gratefully acknowledged.

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Y1 - 2011/10/7

N2 - A concise, stereocontrolled synthesis of the citrinadin B core architecture from scalemic, readily available starting materials is disclosed. Highlights include ready access to both cyclic tryptophan tautomer and trans-2,6- disubstituted piperidine fragments, an efficient, stereoretentive mixed Claisen acylation for the coupling of these halves, and further diastereoselective carbonyl addition and oxidative rearrangement for assembly of the core.

AB - A concise, stereocontrolled synthesis of the citrinadin B core architecture from scalemic, readily available starting materials is disclosed. Highlights include ready access to both cyclic tryptophan tautomer and trans-2,6- disubstituted piperidine fragments, an efficient, stereoretentive mixed Claisen acylation for the coupling of these halves, and further diastereoselective carbonyl addition and oxidative rearrangement for assembly of the core.

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Concise, stereocontrolled synthesis of the citrinadin B core architecture

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