Studies towards total synthesis of antillatoxin: Synthesis of C1-C11 fragment

Teck Peng Loh; Guo Qiang Cao; Jian Pei

doi:10.1016/S0040-4039(97)10827-9

Studies towards total synthesis of antillatoxin: Synthesis of C1-C11 fragment

Teck Peng Loh, Guo Qiang Cao, Jian Pei

National University of Singapore

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42 Scopus citations

Abstract

Synthesis of the key intermediate (5) of Antillatoxin (1) is presented. The synthesis is based on the indium-mediated allylation of 2,4,6,6-tetramethyl-2,4-heptadienal (3) and methyl (Z)-2-(bromomethyl)-2-butenoate (4) in saturated ammonium chloride catalyzed by lanthanide triflate which afforded the corresponding product 2 in good yield and high syn selectivity.

Original language	English
Pages (from-to)	1457-1460
Number of pages	4
Journal	Tetrahedron Letters
Volume	39
Issue number	11
DOIs	https://doi.org/10.1016/S0040-4039(97)10827-9
State	Published - 12 Mar 1998
Externally published	Yes

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title = "Studies towards total synthesis of antillatoxin: Synthesis of C1-C11 fragment",

abstract = "Synthesis of the key intermediate (5) of Antillatoxin (1) is presented. The synthesis is based on the indium-mediated allylation of 2,4,6,6-tetramethyl-2,4-heptadienal (3) and methyl (Z)-2-(bromomethyl)-2-butenoate (4) in saturated ammonium chloride catalyzed by lanthanide triflate which afforded the corresponding product 2 in good yield and high syn selectivity.",

author = "Loh, {Teck Peng} and Cao, {Guo Qiang} and Jian Pei",

year = "1998",

month = mar,

day = "12",

doi = "10.1016/S0040-4039(97)10827-9",

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volume = "39",

pages = "1457--1460",

journal = "Tetrahedron Letters",

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T1 - Studies towards total synthesis of antillatoxin

T2 - Synthesis of C1-C11 fragment

AU - Loh, Teck Peng

AU - Cao, Guo Qiang

AU - Pei, Jian

PY - 1998/3/12

Y1 - 1998/3/12

N2 - Synthesis of the key intermediate (5) of Antillatoxin (1) is presented. The synthesis is based on the indium-mediated allylation of 2,4,6,6-tetramethyl-2,4-heptadienal (3) and methyl (Z)-2-(bromomethyl)-2-butenoate (4) in saturated ammonium chloride catalyzed by lanthanide triflate which afforded the corresponding product 2 in good yield and high syn selectivity.

AB - Synthesis of the key intermediate (5) of Antillatoxin (1) is presented. The synthesis is based on the indium-mediated allylation of 2,4,6,6-tetramethyl-2,4-heptadienal (3) and methyl (Z)-2-(bromomethyl)-2-butenoate (4) in saturated ammonium chloride catalyzed by lanthanide triflate which afforded the corresponding product 2 in good yield and high syn selectivity.

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U2 - 10.1016/S0040-4039(97)10827-9

DO - 10.1016/S0040-4039(97)10827-9

M3 - 文章

AN - SCOPUS:0032510431

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VL - 39

SP - 1457

EP - 1460

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 11

ER -

Studies towards total synthesis of antillatoxin: Synthesis of C1-C11 fragment

Abstract

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