New protocols for the assembly of the tetracyclic framework associated with the aromatic erythrina alkaloids

Pauline C. Stanislawski; Anthony C. Willis; Martin G. Banwell

doi:10.1021/ol060642c

New protocols for the assembly of the tetracyclic framework associated with the aromatic erythrina alkaloids

Pauline C. Stanislawski
, Anthony C. Willis
, Martin G. Banwell^*

^*Corresponding author for this work

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

43 Citations (Scopus)

Abstract

Treatment of the anion derived from the ring-fused gem-dichlorocyclopropane 4c with silver tetrafluoroborate afforded the spirocyclic compound 17 in 74% yield. Product 17 was readily converted, over three steps, into the β-odoethyl derivative 20 and treatment of this latter compound with n-Bu₃SnH then afforded, in 93% yield and via a radical addition/elimination sequence, compound 2 incorporating the ABCD framework of the aromatic erythrina alkaloids.

Original language	English
Pages (from-to)	2143-2146
Number of pages	4
Journal	Organic Letters
Volume	8
Issue number	10
DOIs	https://doi.org/10.1021/ol060642c
Publication status	Published - 11 May 2006

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title = "New protocols for the assembly of the tetracyclic framework associated with the aromatic erythrina alkaloids",

abstract = "Treatment of the anion derived from the ring-fused gem-dichlorocyclopropane 4c with silver tetrafluoroborate afforded the spirocyclic compound 17 in 74\% yield. Product 17 was readily converted, over three steps, into the β-odoethyl derivative 20 and treatment of this latter compound with n-Bu3SnH then afforded, in 93\% yield and via a radical addition/elimination sequence, compound 2 incorporating the ABCD framework of the aromatic erythrina alkaloids.",

author = "Stanislawski, \{Pauline C.\} and Willis, \{Anthony C.\} and Banwell, \{Martin G.\}",

year = "2006",

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journal = "Organic Letters",

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AU - Stanislawski, Pauline C.

AU - Willis, Anthony C.

AU - Banwell, Martin G.

PY - 2006/5/11

Y1 - 2006/5/11

N2 - Treatment of the anion derived from the ring-fused gem-dichlorocyclopropane 4c with silver tetrafluoroborate afforded the spirocyclic compound 17 in 74% yield. Product 17 was readily converted, over three steps, into the β-odoethyl derivative 20 and treatment of this latter compound with n-Bu3SnH then afforded, in 93% yield and via a radical addition/elimination sequence, compound 2 incorporating the ABCD framework of the aromatic erythrina alkaloids.

AB - Treatment of the anion derived from the ring-fused gem-dichlorocyclopropane 4c with silver tetrafluoroborate afforded the spirocyclic compound 17 in 74% yield. Product 17 was readily converted, over three steps, into the β-odoethyl derivative 20 and treatment of this latter compound with n-Bu3SnH then afforded, in 93% yield and via a radical addition/elimination sequence, compound 2 incorporating the ABCD framework of the aromatic erythrina alkaloids.

UR - https://www.scopus.com/pages/publications/33744737931

U2 - 10.1021/ol060642c

DO - 10.1021/ol060642c

M3 - Article

SN - 1523-7060

VL - 8

SP - 2143

EP - 2146

JO - Organic Letters

JF - Organic Letters

IS - 10

ER -

New protocols for the assembly of the tetracyclic framework associated with the aromatic erythrina alkaloids

Abstract

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