PYRYLIUM-SALTS IN POLYENE NATURAL PRODUCT SYNTHESIS - ORGANOMETALLIC ADDITIONS TO 4-METHYLPYRYLIUM TETRAFLUOROBORATE

R J K  TAYLOR; K  HEMMING; E F  DEMEDEIROS

PYRYLIUM-SALTS IN POLYENE NATURAL PRODUCT SYNTHESIS - ORGANOMETALLIC ADDITIONS TO 4-METHYLPYRYLIUM TETRAFLUOROBORATE

R J K TAYLOR, K HEMMING, E F DEMEDEIROS

Chemistry

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

Abstract

The synthetic utility of organometallic additions to pyrylium salts as a procedure for the stereocontrolled preparation of 2Z,4E-dienals, and the use of these compounds in polyene natural product synthesis, is summarised. The extension of this methodology to 4-methylpyrylium tetrafluoroborate to give a new route to 3-methyl-2Z,4E-dienals via a six-carbon organometallic homologation procedure is then described. Finally, the utilisation of this methodology to provide a concise synthetic approach to 13Z-retinal, retinal and a range of retinal analogues is then elaborated.

Original language	English
Pages (from-to)	2385-2392
Number of pages	8
Journal	Journal of the Chemical Society-Perkin Transactions 1
Issue number	19
Publication status	Published - 7 Oct 1995

Keywords

VITAMIN-A
STEREOSELECTIVE SYNTHESIS
ABSOLUTE-CONFIGURATION
UMBRACULUMIN-A
ALDEHYDES
REAGENTS
RETINOIDS
ROUTE
HOMOLOGATION
PERCHLORATE

Cite this

@article{2b386cdb8434449db795da18c6e47fa8,

title = "PYRYLIUM-SALTS IN POLYENE NATURAL PRODUCT SYNTHESIS - ORGANOMETALLIC ADDITIONS TO 4-METHYLPYRYLIUM TETRAFLUOROBORATE",

abstract = "The synthetic utility of organometallic additions to pyrylium salts as a procedure for the stereocontrolled preparation of 2Z,4E-dienals, and the use of these compounds in polyene natural product synthesis, is summarised. The extension of this methodology to 4-methylpyrylium tetrafluoroborate to give a new route to 3-methyl-2Z,4E-dienals via a six-carbon organometallic homologation procedure is then described. Finally, the utilisation of this methodology to provide a concise synthetic approach to 13Z-retinal, retinal and a range of retinal analogues is then elaborated.",

keywords = "VITAMIN-A, STEREOSELECTIVE SYNTHESIS, ABSOLUTE-CONFIGURATION, UMBRACULUMIN-A, ALDEHYDES, REAGENTS, RETINOIDS, ROUTE, HOMOLOGATION, PERCHLORATE",

author = "TAYLOR, {R J K} and K HEMMING and DEMEDEIROS, {E F}",

year = "1995",

month = oct,

day = "7",

language = "English",

pages = "2385--2392",

journal = "Journal of the Chemical Society-Perkin Transactions 1",

issn = "0300-922X",

publisher = "Chemical Society",

number = "19",

}

TY - JOUR

T1 - PYRYLIUM-SALTS IN POLYENE NATURAL PRODUCT SYNTHESIS - ORGANOMETALLIC ADDITIONS TO 4-METHYLPYRYLIUM TETRAFLUOROBORATE

AU - TAYLOR, R J K

AU - HEMMING, K

AU - DEMEDEIROS, E F

PY - 1995/10/7

Y1 - 1995/10/7

N2 - The synthetic utility of organometallic additions to pyrylium salts as a procedure for the stereocontrolled preparation of 2Z,4E-dienals, and the use of these compounds in polyene natural product synthesis, is summarised. The extension of this methodology to 4-methylpyrylium tetrafluoroborate to give a new route to 3-methyl-2Z,4E-dienals via a six-carbon organometallic homologation procedure is then described. Finally, the utilisation of this methodology to provide a concise synthetic approach to 13Z-retinal, retinal and a range of retinal analogues is then elaborated.

AB - The synthetic utility of organometallic additions to pyrylium salts as a procedure for the stereocontrolled preparation of 2Z,4E-dienals, and the use of these compounds in polyene natural product synthesis, is summarised. The extension of this methodology to 4-methylpyrylium tetrafluoroborate to give a new route to 3-methyl-2Z,4E-dienals via a six-carbon organometallic homologation procedure is then described. Finally, the utilisation of this methodology to provide a concise synthetic approach to 13Z-retinal, retinal and a range of retinal analogues is then elaborated.

KW - VITAMIN-A

KW - STEREOSELECTIVE SYNTHESIS

KW - ABSOLUTE-CONFIGURATION

KW - UMBRACULUMIN-A

KW - ALDEHYDES

KW - REAGENTS

KW - RETINOIDS

KW - ROUTE

KW - HOMOLOGATION

KW - PERCHLORATE

M3 - Article

SN - 0300-922X

SP - 2385

EP - 2392

JO - Journal of the Chemical Society-Perkin Transactions 1

JF - Journal of the Chemical Society-Perkin Transactions 1

IS - 19

ER -