Direct, Biomimetic Synthesis of (+)-Artemone via a Stereoselective, Organocatalytic Cyclization

Eric D. Nacsa; Brian C. Fielder; Shannon P. Wetzler; Veerasak Srisuknimit; Jonathan P. Litz; Mary J. Van Vleet; Kim Quach; David A. Vosburg

doi:10.1055/s-0034-1380684

Direct, Biomimetic Synthesis of (+)-Artemone via a Stereoselective, Organocatalytic Cyclization

Eric D. Nacsa, Brian C. Fielder, Shannon P. Wetzler, Veerasak Srisuknimit, Jonathan P. Litz, Mary J. Van Vleet, Kim Quach, David A. Vosburg

Chemistry

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

6 Scopus citations

Abstract

We present a four-step synthesis of (+)-artemone from (-)-linalool, featuring iminium organocatalysis of a doubly diastereoselective conjugate addition reaction. The strategy follows a proposed biosynthetic pathway, rapidly generates stereochemical complexity, uses no protecting groups, and minimizes redox manipulations. Georg Thieme Verlag Stuttgart.

Original language	English (US)
Article number	ss-2015-m0145-op
Pages (from-to)	2599-2602
Number of pages	4
Journal	Synthesis (Germany)
Volume	47
Issue number	17
DOIs	https://doi.org/10.1055/s-0034-1380684
State	Published - Sep 1 2015

All Science Journal Classification (ASJC) codes

Catalysis
Organic Chemistry

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title = "Direct, Biomimetic Synthesis of (+)-Artemone via a Stereoselective, Organocatalytic Cyclization",

abstract = "We present a four-step synthesis of (+)-artemone from (-)-linalool, featuring iminium organocatalysis of a doubly diastereoselective conjugate addition reaction. The strategy follows a proposed biosynthetic pathway, rapidly generates stereochemical complexity, uses no protecting groups, and minimizes redox manipulations. Georg Thieme Verlag Stuttgart.",

author = "Nacsa, \{Eric D.\} and Fielder, \{Brian C.\} and Wetzler, \{Shannon P.\} and Veerasak Srisuknimit and Litz, \{Jonathan P.\} and \{Van Vleet\}, \{Mary J.\} and Kim Quach and Vosburg, \{David A.\}",

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AU - Nacsa, Eric D.

AU - Fielder, Brian C.

AU - Wetzler, Shannon P.

AU - Srisuknimit, Veerasak

AU - Litz, Jonathan P.

AU - Van Vleet, Mary J.

AU - Quach, Kim

AU - Vosburg, David A.

PY - 2015/9/1

Y1 - 2015/9/1

N2 - We present a four-step synthesis of (+)-artemone from (-)-linalool, featuring iminium organocatalysis of a doubly diastereoselective conjugate addition reaction. The strategy follows a proposed biosynthetic pathway, rapidly generates stereochemical complexity, uses no protecting groups, and minimizes redox manipulations. Georg Thieme Verlag Stuttgart.

AB - We present a four-step synthesis of (+)-artemone from (-)-linalool, featuring iminium organocatalysis of a doubly diastereoselective conjugate addition reaction. The strategy follows a proposed biosynthetic pathway, rapidly generates stereochemical complexity, uses no protecting groups, and minimizes redox manipulations. Georg Thieme Verlag Stuttgart.

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DO - 10.1055/s-0034-1380684

M3 - Article

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JF - Synthesis (Germany)

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M1 - ss-2015-m0145-op

ER -

Direct, Biomimetic Synthesis of (+)-Artemone via a Stereoselective, Organocatalytic Cyclization

Abstract

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