A short synthesis of (±)-13-deoxyserratine

Jérome Cassayre; Fabien Gagosz; Samir Z. Zard

doi:10.1002/1521-3773(20020517)41:10<1783::AID-ANIE1783>3.0.CO;2-I

A short synthesis of (±)-13-deoxyserratine

Jérome Cassayre
, Fabien Gagosz
, Samir Z. Zard

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

Abstract

A short and efficient total synthesis of (±)-13-deoxyserratine (3) features a highly stereoselective intramolecular Pauson-Khand reaction of 1 and a cascade of radical cyclizations starting with the amidyl radical 2. The desired alkaloid 3 was thus obtained in ten steps in an overall yield of 12 %. THP = tetrahydropyranyl, TBS = tert-butyldimethylsilyl.

Original language	English
Pages (from-to)	1783-1785
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	41
Issue number	10
DOIs	https://doi.org/10.1002/1521-3773(20020517)41:10<1783::AID-ANIE1783>3.0.CO;2-I
Publication status	Published - 8 Jun 2002

Keywords

Alkaloids
Indolizidines
Pauson-Khand reaction
Radical reactions
Total synthesis

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10.1002/1521-3773(20020517)41:10<1783::AID-ANIE1783>3.0.CO;2-I

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title = "A short synthesis of (±)-13-deoxyserratine",

abstract = "A short and efficient total synthesis of (±)-13-deoxyserratine (3) features a highly stereoselective intramolecular Pauson-Khand reaction of 1 and a cascade of radical cyclizations starting with the amidyl radical 2. The desired alkaloid 3 was thus obtained in ten steps in an overall yield of 12 \%. THP = tetrahydropyranyl, TBS = tert-butyldimethylsilyl.",

keywords = "Alkaloids, Indolizidines, Pauson-Khand reaction, Radical reactions, Total synthesis",

author = "J{\'e}rome Cassayre and Fabien Gagosz and Zard, \{Samir Z.\}",

year = "2002",

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doi = "10.1002/1521-3773(20020517)41:10<1783::AID-ANIE1783>3.0.CO;2-I",

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T1 - A short synthesis of (±)-13-deoxyserratine

AU - Cassayre, Jérome

AU - Gagosz, Fabien

AU - Zard, Samir Z.

PY - 2002/6/8

Y1 - 2002/6/8

N2 - A short and efficient total synthesis of (±)-13-deoxyserratine (3) features a highly stereoselective intramolecular Pauson-Khand reaction of 1 and a cascade of radical cyclizations starting with the amidyl radical 2. The desired alkaloid 3 was thus obtained in ten steps in an overall yield of 12 %. THP = tetrahydropyranyl, TBS = tert-butyldimethylsilyl.

AB - A short and efficient total synthesis of (±)-13-deoxyserratine (3) features a highly stereoselective intramolecular Pauson-Khand reaction of 1 and a cascade of radical cyclizations starting with the amidyl radical 2. The desired alkaloid 3 was thus obtained in ten steps in an overall yield of 12 %. THP = tetrahydropyranyl, TBS = tert-butyldimethylsilyl.

KW - Alkaloids

KW - Indolizidines

KW - Pauson-Khand reaction

KW - Radical reactions

KW - Total synthesis

U2 - 10.1002/1521-3773(20020517)41:10<1783::AID-ANIE1783>3.0.CO;2-I

DO - 10.1002/1521-3773(20020517)41:10<1783::AID-ANIE1783>3.0.CO;2-I

M3 - Article

C2 - 19750716

AN - SCOPUS:0036263802

SN - 1433-7851

VL - 41

SP - 1783

EP - 1785

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 10

ER -

A short synthesis of (±)-13-deoxyserratine

Abstract

Keywords

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