Revisiting a classic approach to the Aspidosperma alkaloids: An intramolecular Schmidt reaction mediated synthesis of (+)-aspidospermidine

Rajesh Iyengar; Klaas Schildknegt; Martha Morton; Jeffrey Aubé

doi:10.1021/jo051212n

Revisiting a classic approach to the Aspidosperma alkaloids: An intramolecular Schmidt reaction mediated synthesis of (+)-aspidospermidine

Rajesh Iyengar, Klaas Schildknegt, Martha Morton, Jeffrey Aubé

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

103 Scopus citations

Abstract

A total synthesis of (+)-aspidospermidine (1) is described. The key reactions used in the synthesis of this pentacyclic Aspidosperma alkaloid were a deracemizing imine alkylation/Robinson annulation sequence, a selective "redox ketalization", and an intramolecular Schmidt reaction. A Fischer indolization step carried out on a tricyclic ketone mirrored the sequence reported by Stork and Dolfini in their classic aspidospermine synthesis.

Original language	English (US)
Pages (from-to)	10645-10652
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	70
Issue number	26
DOIs	https://doi.org/10.1021/jo051212n
State	Published - Dec 23 2005
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1021/jo051212n

Cite this

@article{f63bbdbac6fb468c911df3aa89c4e09f,

title = "Revisiting a classic approach to the Aspidosperma alkaloids: An intramolecular Schmidt reaction mediated synthesis of (+)-aspidospermidine",

abstract = "A total synthesis of (+)-aspidospermidine (1) is described. The key reactions used in the synthesis of this pentacyclic Aspidosperma alkaloid were a deracemizing imine alkylation/Robinson annulation sequence, a selective {"}redox ketalization{"}, and an intramolecular Schmidt reaction. A Fischer indolization step carried out on a tricyclic ketone mirrored the sequence reported by Stork and Dolfini in their classic aspidospermine synthesis.",

author = "Rajesh Iyengar and Klaas Schildknegt and Martha Morton and Jeffrey Aub{\'e}",

year = "2005",

month = dec,

day = "23",

doi = "10.1021/jo051212n",

language = "English (US)",

volume = "70",

pages = "10645--10652",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "26",

}

TY - JOUR

T1 - Revisiting a classic approach to the Aspidosperma alkaloids

T2 - An intramolecular Schmidt reaction mediated synthesis of (+)-aspidospermidine

AU - Iyengar, Rajesh

AU - Schildknegt, Klaas

AU - Morton, Martha

AU - Aubé, Jeffrey

PY - 2005/12/23

Y1 - 2005/12/23

N2 - A total synthesis of (+)-aspidospermidine (1) is described. The key reactions used in the synthesis of this pentacyclic Aspidosperma alkaloid were a deracemizing imine alkylation/Robinson annulation sequence, a selective "redox ketalization", and an intramolecular Schmidt reaction. A Fischer indolization step carried out on a tricyclic ketone mirrored the sequence reported by Stork and Dolfini in their classic aspidospermine synthesis.

AB - A total synthesis of (+)-aspidospermidine (1) is described. The key reactions used in the synthesis of this pentacyclic Aspidosperma alkaloid were a deracemizing imine alkylation/Robinson annulation sequence, a selective "redox ketalization", and an intramolecular Schmidt reaction. A Fischer indolization step carried out on a tricyclic ketone mirrored the sequence reported by Stork and Dolfini in their classic aspidospermine synthesis.

UR - http://www.scopus.com/inward/record.url?scp=29944440165&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=29944440165&partnerID=8YFLogxK

U2 - 10.1021/jo051212n

DO - 10.1021/jo051212n

M3 - Article

C2 - 16355981

AN - SCOPUS:29944440165

SN - 0022-3263

VL - 70

SP - 10645

EP - 10652

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 26

ER -

Revisiting a classic approach to the Aspidosperma alkaloids: An intramolecular Schmidt reaction mediated synthesis of (+)-aspidospermidine

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this