A scalable route to trisubstituted (E)-vinyl bromides

Cheon Gyu Cho; Won Suk Kim; Amos B. Smith

doi:10.1021/ol051376q

A scalable route to trisubstituted (E)-vinyl bromides

Cheon Gyu Cho, Won Suk Kim, Amos B. Smith

Department of Chemistry & Nanoscience

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

15 Scopus citations

Abstract

(Chemical Equation Presented) An effective, readily scalable two-step synthesis of trisubstituted (E)-vinyl bromides involving bromination of α,β-unsaturated lactones followed by hydrolytic fragmentation has been developed. Several trisubstituted (E)-vinyl bromides, including multigram quantities of (+)-(E)-4-bromo-2-methyl-3-pentenol, a synthetic intermediate required for the C(8)-C(11) moieties of (+)-tedanolide (1) and (+)-13-deoxytedanolide (2), illustrate the utility of this protocol.

Original language	English
Pages (from-to)	3569-3572
Number of pages	4
Journal	Organic Letters
Volume	7
Issue number	16
DOIs	https://doi.org/10.1021/ol051376q
State	Published - 4 Aug 2005

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abstract = "(Chemical Equation Presented) An effective, readily scalable two-step synthesis of trisubstituted (E)-vinyl bromides involving bromination of α,β-unsaturated lactones followed by hydrolytic fragmentation has been developed. Several trisubstituted (E)-vinyl bromides, including multigram quantities of (+)-(E)-4-bromo-2-methyl-3-pentenol, a synthetic intermediate required for the C(8)-C(11) moieties of (+)-tedanolide (1) and (+)-13-deoxytedanolide (2), illustrate the utility of this protocol.",

author = "Cho, \{Cheon Gyu\} and Kim, \{Won Suk\} and Smith, \{Amos B.\}",

year = "2005",

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doi = "10.1021/ol051376q",

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T1 - A scalable route to trisubstituted (E)-vinyl bromides

AU - Cho, Cheon Gyu

AU - Kim, Won Suk

AU - Smith, Amos B.

PY - 2005/8/4

Y1 - 2005/8/4

N2 - (Chemical Equation Presented) An effective, readily scalable two-step synthesis of trisubstituted (E)-vinyl bromides involving bromination of α,β-unsaturated lactones followed by hydrolytic fragmentation has been developed. Several trisubstituted (E)-vinyl bromides, including multigram quantities of (+)-(E)-4-bromo-2-methyl-3-pentenol, a synthetic intermediate required for the C(8)-C(11) moieties of (+)-tedanolide (1) and (+)-13-deoxytedanolide (2), illustrate the utility of this protocol.

AB - (Chemical Equation Presented) An effective, readily scalable two-step synthesis of trisubstituted (E)-vinyl bromides involving bromination of α,β-unsaturated lactones followed by hydrolytic fragmentation has been developed. Several trisubstituted (E)-vinyl bromides, including multigram quantities of (+)-(E)-4-bromo-2-methyl-3-pentenol, a synthetic intermediate required for the C(8)-C(11) moieties of (+)-tedanolide (1) and (+)-13-deoxytedanolide (2), illustrate the utility of this protocol.

UR - https://www.scopus.com/pages/publications/23944449038

U2 - 10.1021/ol051376q

DO - 10.1021/ol051376q

M3 - Article

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VL - 7

SP - 3569

EP - 3572

JO - Organic Letters

JF - Organic Letters

IS - 16

ER -

A scalable route to trisubstituted (E)-vinyl bromides

Abstract

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