Enantiospecific Synthesis of (-)-Tabtoxinine β-Lactam

Roland E. Dolle; Chun Sing Li; Riccardo Novelli; Lawrence I. Kruse; Drake Eggleston

doi:10.1021/jo00027a024

Enantiospecific Synthesis of (-)-Tabtoxinine β-Lactam

Roland E. Dolle, Chun Sing Li, Riccardo Novelli, Lawrence I. Kruse, Drake Eggleston

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29 Scopus citations

Abstract

A convergent, 10-step synthesis of optically active tabtoxinine β-lactam [(-)-1] has been described. Key features of the synthetic route include (1) preparation of a new γ-cation amino acid synthon, (-)-4, and its use as an electrophile (3 → 11); (2) the one-pot conversion of methyl sulfide 11 to the Cbz-protected amine 12 via stereoselective sulfilimine rearrangement; and (3) chemoselective lactone ring opening in spiro lactam 15a. Synthons (-)-4 and 3 are available on a semipreparative scale.

Original language	English
Pages (from-to)	128-132
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	57
Issue number	1
DOIs	https://doi.org/10.1021/jo00027a024
State	Published - Jan 1 1992

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title = "Enantiospecific Synthesis of (-)-Tabtoxinine β-Lactam",

abstract = "A convergent, 10-step synthesis of optically active tabtoxinine β-lactam [(-)-1] has been described. Key features of the synthetic route include (1) preparation of a new γ-cation amino acid synthon, (-)-4, and its use as an electrophile (3 → 11); (2) the one-pot conversion of methyl sulfide 11 to the Cbz-protected amine 12 via stereoselective sulfilimine rearrangement; and (3) chemoselective lactone ring opening in spiro lactam 15a. Synthons (-)-4 and 3 are available on a semipreparative scale.",

author = "Dolle, {Roland E.} and Li, {Chun Sing} and Riccardo Novelli and Kruse, {Lawrence I.} and Drake Eggleston",

year = "1992",

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doi = "10.1021/jo00027a024",

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T1 - Enantiospecific Synthesis of (-)-Tabtoxinine β-Lactam

AU - Dolle, Roland E.

AU - Li, Chun Sing

AU - Novelli, Riccardo

AU - Kruse, Lawrence I.

AU - Eggleston, Drake

PY - 1992/1/1

Y1 - 1992/1/1

N2 - A convergent, 10-step synthesis of optically active tabtoxinine β-lactam [(-)-1] has been described. Key features of the synthetic route include (1) preparation of a new γ-cation amino acid synthon, (-)-4, and its use as an electrophile (3 → 11); (2) the one-pot conversion of methyl sulfide 11 to the Cbz-protected amine 12 via stereoselective sulfilimine rearrangement; and (3) chemoselective lactone ring opening in spiro lactam 15a. Synthons (-)-4 and 3 are available on a semipreparative scale.

AB - A convergent, 10-step synthesis of optically active tabtoxinine β-lactam [(-)-1] has been described. Key features of the synthetic route include (1) preparation of a new γ-cation amino acid synthon, (-)-4, and its use as an electrophile (3 → 11); (2) the one-pot conversion of methyl sulfide 11 to the Cbz-protected amine 12 via stereoselective sulfilimine rearrangement; and (3) chemoselective lactone ring opening in spiro lactam 15a. Synthons (-)-4 and 3 are available on a semipreparative scale.

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M3 - Article

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SN - 0022-3263

VL - 57

SP - 128

EP - 132

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 1

ER -

Enantiospecific Synthesis of (-)-Tabtoxinine β-Lactam

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