Progress towards the total synthesis of tedanolide: An efficient assembly of the C1-C11 subunit

Teck Peng Loh; Li Chun Feng

doi:10.1016/S0040-4039(01)01169-8

Progress towards the total synthesis of tedanolide: An efficient assembly of the C₁-C₁₁ subunit

Teck Peng Loh, Li Chun Feng

National University of Singapore

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33 Scopus citations

Abstract

The C₁-C₁₁ subunit of tedanolide was constructed using a boron-mediated syn aldol reaction as the key step to control the C₆ and C₇ stereocenters. Other features of this work include the asymmetric Sharpless dihydroxylation to incorporate the C₂, C₃ hydroxyl groups, selective protection of the hydroxyl group at C₂ as well as the usage of a tert-butyl ester to tolerate the attack of Grignard and enolate reagents.

Original language	English
Pages (from-to)	6001-6005
Number of pages	5
Journal	Tetrahedron Letters
Volume	42
Issue number	34
DOIs	https://doi.org/10.1016/S0040-4039(01)01169-8
State	Published - 20 Aug 2001
Externally published	Yes

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title = "Progress towards the total synthesis of tedanolide: An efficient assembly of the C1-C11 subunit",

abstract = "The C1-C11 subunit of tedanolide was constructed using a boron-mediated syn aldol reaction as the key step to control the C6 and C7 stereocenters. Other features of this work include the asymmetric Sharpless dihydroxylation to incorporate the C2, C3 hydroxyl groups, selective protection of the hydroxyl group at C2 as well as the usage of a tert-butyl ester to tolerate the attack of Grignard and enolate reagents.",

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AU - Feng, Li Chun

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N2 - The C1-C11 subunit of tedanolide was constructed using a boron-mediated syn aldol reaction as the key step to control the C6 and C7 stereocenters. Other features of this work include the asymmetric Sharpless dihydroxylation to incorporate the C2, C3 hydroxyl groups, selective protection of the hydroxyl group at C2 as well as the usage of a tert-butyl ester to tolerate the attack of Grignard and enolate reagents.

AB - The C1-C11 subunit of tedanolide was constructed using a boron-mediated syn aldol reaction as the key step to control the C6 and C7 stereocenters. Other features of this work include the asymmetric Sharpless dihydroxylation to incorporate the C2, C3 hydroxyl groups, selective protection of the hydroxyl group at C2 as well as the usage of a tert-butyl ester to tolerate the attack of Grignard and enolate reagents.

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U2 - 10.1016/S0040-4039(01)01169-8

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JF - Tetrahedron Letters

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ER -

Progress towards the total synthesis of tedanolide: An efficient assembly of the C₁-C₁₁ subunit

Abstract

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