Anodic cyclization reactions and the synthesis of (-)-crobarbatic acid

Hai Chao Xu; John D. Brandt; Kevin D. Moeller

doi:10.1016/j.tetlet.2008.04.075

Anodic cyclization reactions and the synthesis of (-)-crobarbatic acid

Hai Chao Xu
, John D. Brandt
, Kevin D. Moeller

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

46 Scopus citations

Abstract

A synthesis of (-)-crobarbatic acid is reported along with the first use of a vinyl-substituted ketene dithioacetal as a coupling partner for an anodic cyclization reaction. The use of the vinyl-substituted ketene dithioacetal enables the construction of a cyclic product having a tetrasubstituted carbon with a relative stereochemistry opposite to that originally obtained from the cyclization.

Original language	English
Pages (from-to)	3868-3871
Number of pages	4
Journal	Tetrahedron Letters
Volume	49
Issue number	24
DOIs	https://doi.org/10.1016/j.tetlet.2008.04.075
State	Published - Jun 9 2008

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10.1016/j.tetlet.2008.04.075

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title = "Anodic cyclization reactions and the synthesis of (-)-crobarbatic acid",

abstract = "A synthesis of (-)-crobarbatic acid is reported along with the first use of a vinyl-substituted ketene dithioacetal as a coupling partner for an anodic cyclization reaction. The use of the vinyl-substituted ketene dithioacetal enables the construction of a cyclic product having a tetrasubstituted carbon with a relative stereochemistry opposite to that originally obtained from the cyclization.",

author = "Xu, \{Hai Chao\} and Brandt, \{John D.\} and Moeller, \{Kevin D.\}",

note = "Funding Information: We thank the National Science Foundation (CHE-9023698) for their generous support of our work. We also gratefully acknowledge the Washington University High Resolution NMR facility, partially supported by NIH Grants RR02004, RR05018, and RR07155, and the Washington University Mass Spectrometry Resource Center, partially supported by NIHRR00954, for their assistance.",

year = "2008",

month = jun,

day = "9",

doi = "10.1016/j.tetlet.2008.04.075",

language = "English",

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journal = "Tetrahedron Letters",

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T1 - Anodic cyclization reactions and the synthesis of (-)-crobarbatic acid

AU - Xu, Hai Chao

AU - Brandt, John D.

AU - Moeller, Kevin D.

N1 - Funding Information: We thank the National Science Foundation (CHE-9023698) for their generous support of our work. We also gratefully acknowledge the Washington University High Resolution NMR facility, partially supported by NIH Grants RR02004, RR05018, and RR07155, and the Washington University Mass Spectrometry Resource Center, partially supported by NIHRR00954, for their assistance.

PY - 2008/6/9

Y1 - 2008/6/9

N2 - A synthesis of (-)-crobarbatic acid is reported along with the first use of a vinyl-substituted ketene dithioacetal as a coupling partner for an anodic cyclization reaction. The use of the vinyl-substituted ketene dithioacetal enables the construction of a cyclic product having a tetrasubstituted carbon with a relative stereochemistry opposite to that originally obtained from the cyclization.

AB - A synthesis of (-)-crobarbatic acid is reported along with the first use of a vinyl-substituted ketene dithioacetal as a coupling partner for an anodic cyclization reaction. The use of the vinyl-substituted ketene dithioacetal enables the construction of a cyclic product having a tetrasubstituted carbon with a relative stereochemistry opposite to that originally obtained from the cyclization.

UR - https://www.scopus.com/pages/publications/43049173603

U2 - 10.1016/j.tetlet.2008.04.075

DO - 10.1016/j.tetlet.2008.04.075

M3 - Article

AN - SCOPUS:43049173603

SN - 0040-4039

VL - 49

SP - 3868

EP - 3871

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 24

ER -

Anodic cyclization reactions and the synthesis of (-)-crobarbatic acid

Abstract

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