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

^*Corresponding author for this work

National University of Singapore

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

42 Citations (Scopus)

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
Publication status	Published - Mar 12 1998
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

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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",

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

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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 - Article

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EP - 1460

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 11

ER -

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

Abstract

ASJC Scopus Subject Areas

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