A formal synthesis of (±)-physostigmine via 3,3-rearrangement of a bis-enamine

Paulo F. Santos; Natarajan Srinivasan; Paulo S. Almeida; Ana M. Lobo; Sundaresan Prabhakar

doi:10.1016/j.tet.2005.07.030

A formal synthesis of (±)-physostigmine via 3,3-rearrangement of a bis-enamine

Paulo F. Santos, Natarajan Srinivasan, Paulo S. Almeida, Ana M. Lobo, Sundaresan Prabhakar

DQ - Departamento de Química

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

21 Citations (Scopus)

Abstract

A new flexible approach to hexahydropyrrolo[2,3-b]indole system via the [3,3]-sigmatropic rearrangement of 1-(2′-methoxycarbonyl-N- methylvinylamino)skatole, culminating in the synthesis of (±)- desoxyeseroline, is described.

Original language	English
Pages (from-to)	9147-9156
Number of pages	10
Journal	Tetrahedron
Volume	61
Issue number	38
DOIs	https://doi.org/10.1016/j.tet.2005.07.030
Publication status	Published - 19 Sep 2005

Keywords

Enamines
Eseroline
Physostigmine
Sigmatropic rearrangements

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abstract = "A new flexible approach to hexahydropyrrolo[2,3-b]indole system via the [3,3]-sigmatropic rearrangement of 1-(2′-methoxycarbonyl-N- methylvinylamino)skatole, culminating in the synthesis of (±)- desoxyeseroline, is described.",

keywords = "Enamines, Eseroline, Physostigmine, Sigmatropic rearrangements",

author = "Santos, {Paulo F.} and Natarajan Srinivasan and Almeida, {Paulo S.} and Lobo, {Ana M.} and Sundaresan Prabhakar",

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AU - Santos, Paulo F.

AU - Srinivasan, Natarajan

AU - Almeida, Paulo S.

AU - Lobo, Ana M.

AU - Prabhakar, Sundaresan

PY - 2005/9/19

Y1 - 2005/9/19

N2 - A new flexible approach to hexahydropyrrolo[2,3-b]indole system via the [3,3]-sigmatropic rearrangement of 1-(2′-methoxycarbonyl-N- methylvinylamino)skatole, culminating in the synthesis of (±)- desoxyeseroline, is described.

AB - A new flexible approach to hexahydropyrrolo[2,3-b]indole system via the [3,3]-sigmatropic rearrangement of 1-(2′-methoxycarbonyl-N- methylvinylamino)skatole, culminating in the synthesis of (±)- desoxyeseroline, is described.

KW - Enamines

KW - Eseroline

KW - Physostigmine

KW - Sigmatropic rearrangements

UR - http://www.scopus.com/inward/record.url?scp=23944510845&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2005.07.030

DO - 10.1016/j.tet.2005.07.030

M3 - Article

VL - 61

SP - 9147

EP - 9156

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 38

ER -

A formal synthesis of (±)-physostigmine via 3,3-rearrangement of a bis-enamine

Abstract

Keywords

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