THE SYNTHESIS AND ABSOLUTE-CONFIGURATION OF THE NOVEL ICHTHYOTOXIC DIACYLGLYCEROLS, UMBRACULUMIN-A AND UMBRACULUMIN-C

E F  DEMEDEIROS; J M  HERBERT; R J K  TAYLOR

THE SYNTHESIS AND ABSOLUTE-CONFIGURATION OF THE NOVEL ICHTHYOTOXIC DIACYLGLYCEROLS, UMBRACULUMIN-A AND UMBRACULUMIN-C

E F DEMEDEIROS, J M HERBERT, R J K TAYLOR

Chemistry

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

Abstract

The total syntheses of umbraculumin A 1 and umbraculumin C 2 in homochiral form are described. Noteworthy steps involve (i) the preparation of the key Z,E-acid 10 by organolithium addition to pyrylium salts, (ii) the use of the 4-methoxyphenylmethyl protecting group for the preparation of 1,2-diacyl glycerols and its removal using trifluoroacetic acid-anisole without significant acyl migration (DDQ removal having proved inefficient) and (iii) a new procedure for the stereoselective preparation of (Z)- and (E)-3-methylthiopropenoic acid.

Original language	English
Pages (from-to)	2725-2730
Number of pages	6
Journal	Journal of the Chemical Society-Perkin Transactions 1
Issue number	11
Publication status	Published - Nov 1991

Keywords

ICHTHYOTOXIC DIACYLGLYCEROLS
ALKYL IODIDES
MOLLUSKS

Cite this

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title = "THE SYNTHESIS AND ABSOLUTE-CONFIGURATION OF THE NOVEL ICHTHYOTOXIC DIACYLGLYCEROLS, UMBRACULUMIN-A AND UMBRACULUMIN-C",

abstract = "The total syntheses of umbraculumin A 1 and umbraculumin C 2 in homochiral form are described. Noteworthy steps involve (i) the preparation of the key Z,E-acid 10 by organolithium addition to pyrylium salts, (ii) the use of the 4-methoxyphenylmethyl protecting group for the preparation of 1,2-diacyl glycerols and its removal using trifluoroacetic acid-anisole without significant acyl migration (DDQ removal having proved inefficient) and (iii) a new procedure for the stereoselective preparation of (Z)- and (E)-3-methylthiopropenoic acid.",

keywords = "ICHTHYOTOXIC DIACYLGLYCEROLS, ALKYL IODIDES, MOLLUSKS",

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

year = "1991",

month = nov,

language = "English",

pages = "2725--2730",

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

issn = "0300-922X",

publisher = "Chemical Society",

number = "11",

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TY - JOUR

T1 - THE SYNTHESIS AND ABSOLUTE-CONFIGURATION OF THE NOVEL ICHTHYOTOXIC DIACYLGLYCEROLS, UMBRACULUMIN-A AND UMBRACULUMIN-C

AU - DEMEDEIROS, E F

AU - HERBERT, J M

AU - TAYLOR, R J K

PY - 1991/11

Y1 - 1991/11

N2 - The total syntheses of umbraculumin A 1 and umbraculumin C 2 in homochiral form are described. Noteworthy steps involve (i) the preparation of the key Z,E-acid 10 by organolithium addition to pyrylium salts, (ii) the use of the 4-methoxyphenylmethyl protecting group for the preparation of 1,2-diacyl glycerols and its removal using trifluoroacetic acid-anisole without significant acyl migration (DDQ removal having proved inefficient) and (iii) a new procedure for the stereoselective preparation of (Z)- and (E)-3-methylthiopropenoic acid.

AB - The total syntheses of umbraculumin A 1 and umbraculumin C 2 in homochiral form are described. Noteworthy steps involve (i) the preparation of the key Z,E-acid 10 by organolithium addition to pyrylium salts, (ii) the use of the 4-methoxyphenylmethyl protecting group for the preparation of 1,2-diacyl glycerols and its removal using trifluoroacetic acid-anisole without significant acyl migration (DDQ removal having proved inefficient) and (iii) a new procedure for the stereoselective preparation of (Z)- and (E)-3-methylthiopropenoic acid.

KW - ICHTHYOTOXIC DIACYLGLYCEROLS

KW - ALKYL IODIDES

KW - MOLLUSKS

M3 - Article

SN - 0300-922X

SP - 2725

EP - 2730

JO - Journal of the Chemical Society-Perkin Transactions 1

JF - Journal of the Chemical Society-Perkin Transactions 1

IS - 11

ER -