A short synthesis of (+) and (−)-falcarinol

Noel McLaughlin; E. Butler; Paul Evans; Nigel Brunton; Tassos Koidis; Dilip Rai

doi:10.1016/j.tet.2010.10.049

A short synthesis of (+) and (−)-falcarinol

Noel McLaughlin, E. Butler, Paul Evans, Nigel Brunton, Tassos Koidis, Dilip Rai

School of Biological Sciences

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

15 Citations (Scopus)

Abstract

A short, practical synthesis of the bis-acetylenic natural product falcarinol 1 is reported. This method relies on the alternate functionalisation of bis-trimethylsilylbutadiyne 10. This may be achieved in one-pot, however, better yields were obtained more conventionally. Lipase mediated enzymatic kinetic resolution of the racemic adduct in an organic solvent afforded (+)-1 in 97% enantiomeric excess. The analogous process performed with racemic 3-acetoxy falcarinol 11 under aqueous conditions gave (-)-1. Oxidation of 1 with Dess–Martin periodinane gave falcarinone 2.

Original language	English
Pages (from-to)	9681-9687
Number of pages	7
Journal	Tetrahedron
Volume	66(51)
Issue number	51
DOIs	https://doi.org/10.1016/j.tet.2010.10.049
Publication status	Published - 18 Dec 2011

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

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title = "A short synthesis of (+) and (−)-falcarinol",

abstract = "A short, practical synthesis of the bis-acetylenic natural product falcarinol 1 is reported. This method relies on the alternate functionalisation of bis-trimethylsilylbutadiyne 10. This may be achieved in one-pot, however, better yields were obtained more conventionally. Lipase mediated enzymatic kinetic resolution of the racemic adduct in an organic solvent afforded (+)-1 in 97% enantiomeric excess. The analogous process performed with racemic 3-acetoxy falcarinol 11 under aqueous conditions gave (-)-1. Oxidation of 1 with Dess–Martin periodinane gave falcarinone 2.",

author = "Noel McLaughlin and E. Butler and Paul Evans and Nigel Brunton and Tassos Koidis and Dilip Rai",

year = "2011",

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language = "English",

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T1 - A short synthesis of (+) and (−)-falcarinol

AU - McLaughlin, Noel

AU - Butler, E.

AU - Evans, Paul

AU - Brunton, Nigel

AU - Koidis, Tassos

AU - Rai, Dilip

PY - 2011/12/18

Y1 - 2011/12/18

N2 - A short, practical synthesis of the bis-acetylenic natural product falcarinol 1 is reported. This method relies on the alternate functionalisation of bis-trimethylsilylbutadiyne 10. This may be achieved in one-pot, however, better yields were obtained more conventionally. Lipase mediated enzymatic kinetic resolution of the racemic adduct in an organic solvent afforded (+)-1 in 97% enantiomeric excess. The analogous process performed with racemic 3-acetoxy falcarinol 11 under aqueous conditions gave (-)-1. Oxidation of 1 with Dess–Martin periodinane gave falcarinone 2.

AB - A short, practical synthesis of the bis-acetylenic natural product falcarinol 1 is reported. This method relies on the alternate functionalisation of bis-trimethylsilylbutadiyne 10. This may be achieved in one-pot, however, better yields were obtained more conventionally. Lipase mediated enzymatic kinetic resolution of the racemic adduct in an organic solvent afforded (+)-1 in 97% enantiomeric excess. The analogous process performed with racemic 3-acetoxy falcarinol 11 under aqueous conditions gave (-)-1. Oxidation of 1 with Dess–Martin periodinane gave falcarinone 2.

U2 - 10.1016/j.tet.2010.10.049

DO - 10.1016/j.tet.2010.10.049

M3 - Article

VL - 66(51)

SP - 9681

EP - 9687

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 51

ER -