Synthesis of (+)-methyl (R, E)-6-benzyloxy-4-hydroxy-2-hexenoate and its mesylate derivative

Pedro de March; Marta Figueredo; Josep Font; Montserrat Monsalvatje

doi:10.1080/00397919508011364

Synthesis of (+)-methyl (R, E)-6-benzyloxy-4-hydroxy-2-hexenoate and its mesylate derivative

Pedro de March, Marta Figueredo, Josep Font, Montserrat Monsalvatje

Department of Chemistry

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

6 Citations (Scopus)

Abstract

Methyl (E)-6-benzyloxy-4-hydroxy-2-hexenoate is prepared in both racemic and enantiopure form through reaction between (2-benzyloxy)ethyloxirane and the dianion of phenylselenoacetic acid followed by esterification with diazomethane, oxidation to the selenoxide and subsequent pyrolysis in 72% overall yield. © 1995, Taylor & Francis Group, LLC. All rights reserved.

Original language	English
Pages (from-to)	331-342
Journal	Synthetic Communications
Volume	25
Issue number	3
DOIs	https://doi.org/10.1080/00397919508011364
Publication status	Published - 1 Feb 1995

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title = "Synthesis of (+)-methyl (R, E)-6-benzyloxy-4-hydroxy-2-hexenoate and its mesylate derivative",

abstract = "Methyl (E)-6-benzyloxy-4-hydroxy-2-hexenoate is prepared in both racemic and enantiopure form through reaction between (2-benzyloxy)ethyloxirane and the dianion of phenylselenoacetic acid followed by esterification with diazomethane, oxidation to the selenoxide and subsequent pyrolysis in 72% overall yield. {\textcopyright} 1995, Taylor & Francis Group, LLC. All rights reserved.",

author = "{de March}, Pedro and Marta Figueredo and Josep Font and Montserrat Monsalvatje",

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T1 - Synthesis of (+)-methyl (R, E)-6-benzyloxy-4-hydroxy-2-hexenoate and its mesylate derivative

AU - de March, Pedro

AU - Figueredo, Marta

AU - Font, Josep

AU - Monsalvatje, Montserrat

PY - 1995/2/1

Y1 - 1995/2/1

N2 - Methyl (E)-6-benzyloxy-4-hydroxy-2-hexenoate is prepared in both racemic and enantiopure form through reaction between (2-benzyloxy)ethyloxirane and the dianion of phenylselenoacetic acid followed by esterification with diazomethane, oxidation to the selenoxide and subsequent pyrolysis in 72% overall yield. © 1995, Taylor & Francis Group, LLC. All rights reserved.

AB - Methyl (E)-6-benzyloxy-4-hydroxy-2-hexenoate is prepared in both racemic and enantiopure form through reaction between (2-benzyloxy)ethyloxirane and the dianion of phenylselenoacetic acid followed by esterification with diazomethane, oxidation to the selenoxide and subsequent pyrolysis in 72% overall yield. © 1995, Taylor & Francis Group, LLC. All rights reserved.

U2 - 10.1080/00397919508011364

DO - 10.1080/00397919508011364

M3 - Article

SN - 0039-7911

VL - 25

SP - 331

EP - 342

JO - Synthetic Communications

JF - Synthetic Communications

IS - 3

ER -

Synthesis of (+)-methyl (R, E)-6-benzyloxy-4-hydroxy-2-hexenoate and its mesylate derivative

Abstract

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