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

Résultats de recherche: Contribution à un journal › Article › Revue par des pairs

Résumé

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.

langue originale	Anglais
Pages (de - à)	1783-1785
Nombre de pages	3
journal	Angewandte Chemie - International Edition
Volume	41
Numéro de publication	10
Les DOIs	https://doi.org/10.1002/1521-3773(20020517)41:10<1783::AID-ANIE1783>3.0.CO;2-I
état	Publié - 8 juin 2002

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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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AU - Cassayre, Jérome

AU - Gagosz, Fabien

AU - Zard, Samir Z.

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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

UR - https://www.scopus.com/pages/publications/0036263802

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

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AN - SCOPUS:0036263802

SN - 1433-7851

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SP - 1783

EP - 1785

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 10

ER -

A short synthesis of (±)-13-deoxyserratine

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