A raney-cobalt-mediated tandem reductive cyclization route to the 1,5-methanoazocino[4,3-b]indole framework of the uleine and strychnos alkaloids

Tristan A. Reekie; Martin G. Banwell; Anthony C. Willis

doi:10.1021/jo302132d

A raney-cobalt-mediated tandem reductive cyclization route to the 1,5-methanoazocino[4,3-b]indole framework of the uleine and strychnos alkaloids

Tristan A. Reekie, Martin G. Banwell^*, Anthony C. Willis

^*Corresponding author for this work

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

31 Citations (Scopus)

Abstract

The readily accessible enones 8, 17, and 18 undergo 2-fold reductive cyclization reactions upon exposure to hydrogen in the presence of Raney-cobalt and thereby afford compounds 11 (72%), 19 (47%), and 20 (84%), respectively. These products embody the ABCD-ring system associated with the title alkaloids, and compound 11 can be converted, over four steps and in 33% yield, into congener 24 incorporating the ABCDE-ring system of the Strychnos alkaloids.

Original language	English
Pages (from-to)	10773-10781
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	77
Issue number	23
DOIs	https://doi.org/10.1021/jo302132d
Publication status	Published - 7 Dec 2012

Access to Document

10.1021/jo302132d

Cite this

@article{d3a3fddc574941d3ace0b8626d74e87d,

title = "A raney-cobalt-mediated tandem reductive cyclization route to the 1,5-methanoazocino[4,3-b]indole framework of the uleine and strychnos alkaloids",

abstract = "The readily accessible enones 8, 17, and 18 undergo 2-fold reductive cyclization reactions upon exposure to hydrogen in the presence of Raney-cobalt and thereby afford compounds 11 (72%), 19 (47%), and 20 (84%), respectively. These products embody the ABCD-ring system associated with the title alkaloids, and compound 11 can be converted, over four steps and in 33% yield, into congener 24 incorporating the ABCDE-ring system of the Strychnos alkaloids.",

author = "Reekie, {Tristan A.} and Banwell, {Martin G.} and Willis, {Anthony C.}",

year = "2012",

month = dec,

day = "7",

doi = "10.1021/jo302132d",

language = "English",

volume = "77",

pages = "10773--10781",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "23",

}

TY - JOUR

T1 - A raney-cobalt-mediated tandem reductive cyclization route to the 1,5-methanoazocino[4,3-b]indole framework of the uleine and strychnos alkaloids

AU - Reekie, Tristan A.

AU - Banwell, Martin G.

AU - Willis, Anthony C.

PY - 2012/12/7

Y1 - 2012/12/7

N2 - The readily accessible enones 8, 17, and 18 undergo 2-fold reductive cyclization reactions upon exposure to hydrogen in the presence of Raney-cobalt and thereby afford compounds 11 (72%), 19 (47%), and 20 (84%), respectively. These products embody the ABCD-ring system associated with the title alkaloids, and compound 11 can be converted, over four steps and in 33% yield, into congener 24 incorporating the ABCDE-ring system of the Strychnos alkaloids.

AB - The readily accessible enones 8, 17, and 18 undergo 2-fold reductive cyclization reactions upon exposure to hydrogen in the presence of Raney-cobalt and thereby afford compounds 11 (72%), 19 (47%), and 20 (84%), respectively. These products embody the ABCD-ring system associated with the title alkaloids, and compound 11 can be converted, over four steps and in 33% yield, into congener 24 incorporating the ABCDE-ring system of the Strychnos alkaloids.

UR - http://www.scopus.com/inward/record.url?scp=84870874016&partnerID=8YFLogxK

U2 - 10.1021/jo302132d

DO - 10.1021/jo302132d

M3 - Article

SN - 0022-3263

VL - 77

SP - 10773

EP - 10781

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 23

ER -

A raney-cobalt-mediated tandem reductive cyclization route to the 1,5-methanoazocino[4,3-b]indole framework of the uleine and strychnos alkaloids

Abstract

Access to Document

Other files and links

Fingerprint

Cite this