Synthesis of 4, 6-dialkyl-1,3-dioxins. Versatile intermidiates for the preparation of (E)-alkenones, anti,anti-1, 2, 3-triols and syn-1, 3-diols

Raymond L. Funk; Gary L. Bolton

doi:10.1016/S0040-4039(00)86663-0

Synthesis of 4, 6-dialkyl-1,3-dioxins. Versatile intermidiates for the preparation of (E)-alkenones, anti,anti-1, 2, 3-triols and syn-1, 3-diols

Raymond L. Funk
, Gary L. Bolton

Chemistry

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

15 Scopus citations

Abstract

The title compounds 4 are prepared from 4-alkyldioxins 2 via a metalation, alkylation sequence. The dialkyl dioxins 4 are thermally labile (providing enones) and undergo highly stereoselective hydroboration or hydrogenation reactions to provide anti, anti-1, 2, 3-triols and syn, 1, 3-diols, respectively. This methodology has been exploited in the synthesis of (±)-endo-1, 3-dimethyl-2,9-dioxabicyclo[3.3.1]nonane.

Original language	English (US)
Pages (from-to)	1111-1114
Number of pages	4
Journal	Tetrahedron Letters
Volume	29
Issue number	10
DOIs	https://doi.org/10.1016/S0040-4039(00)86663-0
State	Published - 1988

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(00)86663-0

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@article{c151406e26a3436b959962cfa00cbfe4,

title = "Synthesis of 4, 6-dialkyl-1,3-dioxins. Versatile intermidiates for the preparation of (E)-alkenones, anti,anti-1, 2, 3-triols and syn-1, 3-diols",

abstract = "The title compounds 4 are prepared from 4-alkyldioxins 2 via a metalation, alkylation sequence. The dialkyl dioxins 4 are thermally labile (providing enones) and undergo highly stereoselective hydroboration or hydrogenation reactions to provide anti, anti-1, 2, 3-triols and syn, 1, 3-diols, respectively. This methodology has been exploited in the synthesis of (±)-endo-1, 3-dimethyl-2,9-dioxabicyclo[3.3.1]nonane.",

author = "Funk, \{Raymond L.\} and Bolton, \{Gary L.\}",

note = "Funding Information: Acknowledgment.W e thank the National Science Foundation (CHR-8205144)N, ational Institutes of Health (GM-28663),a nd Eli Lilly and Company for financial support.H igh-field (360M Hz) 1H and 1sC NMR spectraw ere obtained on a spectrometerp urchasedw ith funds provided, in part, by the National Science Foundation (CHK80-24328) ; mass spectraw ere obtained through the National Science FoundationR egionalM ass SpectroscopyC enter at the Universityo f Nebraska (CHK-82-11164).",

year = "1988",

doi = "10.1016/S0040-4039(00)86663-0",

language = "English (US)",

volume = "29",

pages = "1111--1114",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "10",

}

TY - JOUR

T1 - Synthesis of 4, 6-dialkyl-1,3-dioxins. Versatile intermidiates for the preparation of (E)-alkenones, anti,anti-1, 2, 3-triols and syn-1, 3-diols

AU - Funk, Raymond L.

AU - Bolton, Gary L.

N1 - Funding Information: Acknowledgment.W e thank the National Science Foundation (CHR-8205144)N, ational Institutes of Health (GM-28663),a nd Eli Lilly and Company for financial support.H igh-field (360M Hz) 1H and 1sC NMR spectraw ere obtained on a spectrometerp urchasedw ith funds provided, in part, by the National Science Foundation (CHK80-24328) ; mass spectraw ere obtained through the National Science FoundationR egionalM ass SpectroscopyC enter at the Universityo f Nebraska (CHK-82-11164).

PY - 1988

Y1 - 1988

N2 - The title compounds 4 are prepared from 4-alkyldioxins 2 via a metalation, alkylation sequence. The dialkyl dioxins 4 are thermally labile (providing enones) and undergo highly stereoselective hydroboration or hydrogenation reactions to provide anti, anti-1, 2, 3-triols and syn, 1, 3-diols, respectively. This methodology has been exploited in the synthesis of (±)-endo-1, 3-dimethyl-2,9-dioxabicyclo[3.3.1]nonane.

AB - The title compounds 4 are prepared from 4-alkyldioxins 2 via a metalation, alkylation sequence. The dialkyl dioxins 4 are thermally labile (providing enones) and undergo highly stereoselective hydroboration or hydrogenation reactions to provide anti, anti-1, 2, 3-triols and syn, 1, 3-diols, respectively. This methodology has been exploited in the synthesis of (±)-endo-1, 3-dimethyl-2,9-dioxabicyclo[3.3.1]nonane.

UR - https://www.scopus.com/pages/publications/0002499158

UR - https://www.scopus.com/pages/publications/0002499158#tab=citedBy

U2 - 10.1016/S0040-4039(00)86663-0

DO - 10.1016/S0040-4039(00)86663-0

M3 - Article

AN - SCOPUS:0002499158

SN - 0040-4039

VL - 29

SP - 1111

EP - 1114

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 10

ER -

Synthesis of 4, 6-dialkyl-1,3-dioxins. Versatile intermidiates for the preparation of (E)-alkenones, anti,anti-1, 2, 3-triols and syn-1, 3-diols

Abstract

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