Formal synthesis of (±)-peduncularine: Use of the [3 + 2] annulation of allylic silanes and chlorosulfonyl isocyanate

Claudia W. Roberson; K. A. Woerpel

doi:10.1021/ol9913744

Formal synthesis of (±)-peduncularine: Use of the [3 + 2] annulation of allylic silanes and chlorosulfonyl isocyanate

Claudia W. Roberson, K. A. Woerpel

Chemistry

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Abstract

(equation presented) The formal synthesis of the alkaloid (±)-peduncularine (1) was accomplished through the use of a [3 + 2] allylic silane annulation. The annulation of cyclohexadienyl silane 6 with chlorosulfonyl isocyanate followed by an in situ reduction provided bicyclic lactam 7. Conversion of this intermediate to 2 in three steps completed the formal synthesis of (±)-peduncularine.

Original language	English (US)
Pages (from-to)	621-622
Number of pages	2
Journal	Organic Letters
Volume	2
Issue number	5
DOIs	https://doi.org/10.1021/ol9913744
State	Published - Mar 9 2000

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol9913744

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title = "Formal synthesis of (±)-peduncularine: Use of the [3 + 2] annulation of allylic silanes and chlorosulfonyl isocyanate",

abstract = "(equation presented) The formal synthesis of the alkaloid (±)-peduncularine (1) was accomplished through the use of a [3 + 2] allylic silane annulation. The annulation of cyclohexadienyl silane 6 with chlorosulfonyl isocyanate followed by an in situ reduction provided bicyclic lactam 7. Conversion of this intermediate to 2 in three steps completed the formal synthesis of (±)-peduncularine.",

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year = "2000",

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AU - Woerpel, K. A.

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Y1 - 2000/3/9

N2 - (equation presented) The formal synthesis of the alkaloid (±)-peduncularine (1) was accomplished through the use of a [3 + 2] allylic silane annulation. The annulation of cyclohexadienyl silane 6 with chlorosulfonyl isocyanate followed by an in situ reduction provided bicyclic lactam 7. Conversion of this intermediate to 2 in three steps completed the formal synthesis of (±)-peduncularine.

AB - (equation presented) The formal synthesis of the alkaloid (±)-peduncularine (1) was accomplished through the use of a [3 + 2] allylic silane annulation. The annulation of cyclohexadienyl silane 6 with chlorosulfonyl isocyanate followed by an in situ reduction provided bicyclic lactam 7. Conversion of this intermediate to 2 in three steps completed the formal synthesis of (±)-peduncularine.

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Formal synthesis of (±)-peduncularine: Use of the [3 + 2] annulation of allylic silanes and chlorosulfonyl isocyanate

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