Palladium-mediated reductive coupling, a stereoselective approach to the 8-dehydropumiliotoxin skeleton

Stephanie A. Feutran; Helena McAlonan; Paul Stevenson; Andrew D. Walker

doi:10.1016/j.tetlet.2009.03.122

Palladium-mediated reductive coupling, a stereoselective approach to the 8-dehydropumiliotoxin skeleton

Stephanie A. Feutran, Helena McAlonan, Paul Stevenson, Andrew D. Walker

School of Chemistry and Chemical Engineering

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

3 Citations (Scopus)

Abstract

Reductive cyclisation of ail E-vinyl bromide with ail allylic acetate proceeds under palladium catalysis 10 give the 8-dehydropumiliotoxin skeleton, a potential advanced precursor to 8-deoxypumiliotoxin alkaloids. Control of the stereochemistry of the E-vinyl bromide precursor is achieved readily using the Kogen or Bruckner bromophosphonate reagents and the reductive cyclisation proceeds with retention of the vinyl bromide stereochemistry. The mechanism for the cyclisation involves an in situ conversion of the allylic acetate to ail allyl stannane followed by ail intramolecular Stille-type coupling.

Original language	English
Pages (from-to)	3669-3671
Number of pages	3
Journal	Tetrahedron Letters
Volume	50
Issue number	26
DOIs	https://doi.org/10.1016/j.tetlet.2009.03.122
Publication status	Published - 01 Jul 2009

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

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title = "Palladium-mediated reductive coupling, a stereoselective approach to the 8-dehydropumiliotoxin skeleton",

abstract = "Reductive cyclisation of ail E-vinyl bromide with ail allylic acetate proceeds under palladium catalysis 10 give the 8-dehydropumiliotoxin skeleton, a potential advanced precursor to 8-deoxypumiliotoxin alkaloids. Control of the stereochemistry of the E-vinyl bromide precursor is achieved readily using the Kogen or Bruckner bromophosphonate reagents and the reductive cyclisation proceeds with retention of the vinyl bromide stereochemistry. The mechanism for the cyclisation involves an in situ conversion of the allylic acetate to ail allyl stannane followed by ail intramolecular Stille-type coupling.",

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T1 - Palladium-mediated reductive coupling, a stereoselective approach to the 8-dehydropumiliotoxin skeleton

AU - Feutran, Stephanie A.

AU - McAlonan, Helena

AU - Stevenson, Paul

AU - Walker, Andrew D.

PY - 2009/7/1

Y1 - 2009/7/1

N2 - Reductive cyclisation of ail E-vinyl bromide with ail allylic acetate proceeds under palladium catalysis 10 give the 8-dehydropumiliotoxin skeleton, a potential advanced precursor to 8-deoxypumiliotoxin alkaloids. Control of the stereochemistry of the E-vinyl bromide precursor is achieved readily using the Kogen or Bruckner bromophosphonate reagents and the reductive cyclisation proceeds with retention of the vinyl bromide stereochemistry. The mechanism for the cyclisation involves an in situ conversion of the allylic acetate to ail allyl stannane followed by ail intramolecular Stille-type coupling.

AB - Reductive cyclisation of ail E-vinyl bromide with ail allylic acetate proceeds under palladium catalysis 10 give the 8-dehydropumiliotoxin skeleton, a potential advanced precursor to 8-deoxypumiliotoxin alkaloids. Control of the stereochemistry of the E-vinyl bromide precursor is achieved readily using the Kogen or Bruckner bromophosphonate reagents and the reductive cyclisation proceeds with retention of the vinyl bromide stereochemistry. The mechanism for the cyclisation involves an in situ conversion of the allylic acetate to ail allyl stannane followed by ail intramolecular Stille-type coupling.

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U2 - 10.1016/j.tetlet.2009.03.122

DO - 10.1016/j.tetlet.2009.03.122

M3 - Article

VL - 50

SP - 3669

EP - 3671

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 26

ER -