Synthesis of the Tetrahydropyran Fragment of Bistramide D

Roderick W. Bates; Lu Li; Kalpana Palani; Wanida Phetsang; Joanna Kejun Loh

doi:10.1002/ajoc.201402052

Synthesis of the Tetrahydropyran Fragment of Bistramide D

Roderick W. Bates^*, Lu Li, Kalpana Palani, Wanida Phetsang, Joanna Kejun Loh

^*Corresponding author for this work

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

16 Citations (Scopus)

Abstract

A synthesis of the tetrahydropyran (THP) moiety of bistramideD has been completed by using cross-metathesis and kinetically controlled intramolecular oxa-Michael addition to form the ring with excellent trans selectivity. The C9 methyl substituent was introduced by using an unsaturated sulfone building block, which can be most effectively prepared through a combination of diastereoselective allylation and alkene isomerisation. The effect of this methyl group on subsequent cross-metathesis reactions can be mitigated by careful choice of reaction conditions.

Original language	English
Pages (from-to)	792-796
Number of pages	5
Journal	Asian Journal of Organic Chemistry
Volume	3
Issue number	7
DOIs	https://doi.org/10.1002/ajoc.201402052
Publication status	Published - Jul 2014
Externally published	Yes

ASJC Scopus Subject Areas

Organic Chemistry

Keywords

Bistramide D
Metathesis
Oxa-Michael addition
Sulfones
Tetrahydropyrans

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abstract = "A synthesis of the tetrahydropyran (THP) moiety of bistramideD has been completed by using cross-metathesis and kinetically controlled intramolecular oxa-Michael addition to form the ring with excellent trans selectivity. The C9 methyl substituent was introduced by using an unsaturated sulfone building block, which can be most effectively prepared through a combination of diastereoselective allylation and alkene isomerisation. The effect of this methyl group on subsequent cross-metathesis reactions can be mitigated by careful choice of reaction conditions.",

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year = "2014",

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T1 - Synthesis of the Tetrahydropyran Fragment of Bistramide D

AU - Bates, Roderick W.

AU - Li, Lu

AU - Palani, Kalpana

AU - Phetsang, Wanida

AU - Loh, Joanna Kejun

PY - 2014/7

Y1 - 2014/7

N2 - A synthesis of the tetrahydropyran (THP) moiety of bistramideD has been completed by using cross-metathesis and kinetically controlled intramolecular oxa-Michael addition to form the ring with excellent trans selectivity. The C9 methyl substituent was introduced by using an unsaturated sulfone building block, which can be most effectively prepared through a combination of diastereoselective allylation and alkene isomerisation. The effect of this methyl group on subsequent cross-metathesis reactions can be mitigated by careful choice of reaction conditions.

AB - A synthesis of the tetrahydropyran (THP) moiety of bistramideD has been completed by using cross-metathesis and kinetically controlled intramolecular oxa-Michael addition to form the ring with excellent trans selectivity. The C9 methyl substituent was introduced by using an unsaturated sulfone building block, which can be most effectively prepared through a combination of diastereoselective allylation and alkene isomerisation. The effect of this methyl group on subsequent cross-metathesis reactions can be mitigated by careful choice of reaction conditions.

KW - Bistramide D

KW - Metathesis

KW - Oxa-Michael addition

KW - Sulfones

KW - Tetrahydropyrans

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DO - 10.1002/ajoc.201402052

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AN - SCOPUS:84903777289

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JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

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ER -

Synthesis of the Tetrahydropyran Fragment of Bistramide D

Abstract

ASJC Scopus Subject Areas

Keywords

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