An enantioselective total synthesis of (+)-picrasin B

Kenji Kawada; Moonsun Kim; David S. Watt

doi:10.1016/S0040-4039(01)93835-3

An enantioselective total synthesis of (+)-picrasin B

Kenji Kawada, Moonsun Kim, David S. Watt

Molecular and Cellular Biochemistry

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

8 Scopus citations

Abstract

An enantioselective total synthesis of (+)-picrasin B (1) from the R-(-)-enantiomer of the Wieland-Miescher ketone (4) employed an A-AB-ABC-ABCD sequence to assemble the tetracyclic skeleton and relied upon a free radical cyclization of an α-bromoacetal to an enone in order to introduce the D ring and a manganese(III) acetate oxidation of a tricyclic enone intermediate in order to introduce the C-11 oxygen substituent.

Original language	English
Pages (from-to)	5989-5992
Number of pages	4
Journal	Tetrahedron Letters
Volume	30
Issue number	44
DOIs	https://doi.org/10.1016/S0040-4039(01)93835-3
State	Published - 1989

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(01)93835-3

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abstract = "An enantioselective total synthesis of (+)-picrasin B (1) from the R-(-)-enantiomer of the Wieland-Miescher ketone (4) employed an A-AB-ABC-ABCD sequence to assemble the tetracyclic skeleton and relied upon a free radical cyclization of an α-bromoacetal to an enone in order to introduce the D ring and a manganese(III) acetate oxidation of a tricyclic enone intermediate in order to introduce the C-11 oxygen substituent.",

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T1 - An enantioselective total synthesis of (+)-picrasin B

AU - Kawada, Kenji

AU - Kim, Moonsun

AU - Watt, David S.

PY - 1989

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N2 - An enantioselective total synthesis of (+)-picrasin B (1) from the R-(-)-enantiomer of the Wieland-Miescher ketone (4) employed an A-AB-ABC-ABCD sequence to assemble the tetracyclic skeleton and relied upon a free radical cyclization of an α-bromoacetal to an enone in order to introduce the D ring and a manganese(III) acetate oxidation of a tricyclic enone intermediate in order to introduce the C-11 oxygen substituent.

AB - An enantioselective total synthesis of (+)-picrasin B (1) from the R-(-)-enantiomer of the Wieland-Miescher ketone (4) employed an A-AB-ABC-ABCD sequence to assemble the tetracyclic skeleton and relied upon a free radical cyclization of an α-bromoacetal to an enone in order to introduce the D ring and a manganese(III) acetate oxidation of a tricyclic enone intermediate in order to introduce the C-11 oxygen substituent.

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ER -

An enantioselective total synthesis of (+)-picrasin B

Abstract

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