Synthesis of the Originally Proposed Structure of Palmerolide C

Gordon John Florence; Joanna Wlochal

doi:10.1002/chem.201203067

Synthesis of the Originally Proposed Structure of Palmerolide C

Gordon John Florence
, Joanna Wlochal

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

Abstract

A stereoselective synthesis of the proposed structure of palmerolide C (2), a cytotoxic marine macrolide isolated from the Antarctic tunicate Synoicum adareanum, utilizes a convergent carbonyl-based coupling strategy to construct the C1-C24 carbon skeleton. Compound 2 was shown to be a diastereomer of palmerolide C, and the structural revision of the natural product is proposed.

Original language	English
Pages (from-to)	14250-14254
Number of pages	5
Journal	Chemistry - A European Journal
Volume	18
Issue number	45
DOIs	https://doi.org/10.1002/chem.201203067
Publication status	Published - 5 Nov 2012

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 14 Life Below Water

Keywords

REVISED STRUCTURES
VINYLOGOUS ALDOL
structure elucidation
natural products
melanoma
CHEMICAL-SYNTHESIS
FRAGMENT
total synthesis
COUPLING-CONSTANTS
macrolide
TUNICATE SYNOICUM-ADAREANUM
ACYCLIC STRUCTURES
NATURAL-PRODUCTS
FORMAL TOTAL-SYNTHESIS
BIOLOGICAL EVALUATION

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RS Uni Research Fellowship Renewal 2010: University Research Fellowship - New Methods and Strategies for the Synthesis of Bioactive Natural Products
Florence, G. (PI)
1/10/10 → 30/09/13
Project: Fellowship
Synthesis of Palmerolides EP/F011458/1: Synthesis of the Palmerolides
Florence, G. (PI)
EPSRC
1/11/07 → 30/04/11
Project: Standard
The Royal Society 516002.K501/kk: Dr G Florence research fellowship application - 2005
Florence, G. (PI)
The Royal Society
1/10/05 → 30/09/10
Project: Fellowship

Cite this

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title = "Synthesis of the Originally Proposed Structure of Palmerolide C",

abstract = "A stereoselective synthesis of the proposed structure of palmerolide C (2), a cytotoxic marine macrolide isolated from the Antarctic tunicate Synoicum adareanum, utilizes a convergent carbonyl-based coupling strategy to construct the C1-C24 carbon skeleton. Compound 2 was shown to be a diastereomer of palmerolide C, and the structural revision of the natural product is proposed.",

keywords = "REVISED STRUCTURES, VINYLOGOUS ALDOL, structure elucidation, natural products, melanoma, CHEMICAL-SYNTHESIS, FRAGMENT, total synthesis, COUPLING-CONSTANTS, macrolide, TUNICATE SYNOICUM-ADAREANUM, ACYCLIC STRUCTURES, NATURAL-PRODUCTS, FORMAL TOTAL-SYNTHESIS, BIOLOGICAL EVALUATION",

author = "Florence, \{Gordon John\} and Joanna Wlochal",

year = "2012",

month = nov,

day = "5",

doi = "10.1002/chem.201203067",

language = "English",

volume = "18",

pages = "14250--14254",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "John Wiley \& Sons, Ltd",

number = "45",

}

TY - JOUR

T1 - Synthesis of the Originally Proposed Structure of Palmerolide C

AU - Florence, Gordon John

AU - Wlochal, Joanna

PY - 2012/11/5

Y1 - 2012/11/5

N2 - A stereoselective synthesis of the proposed structure of palmerolide C (2), a cytotoxic marine macrolide isolated from the Antarctic tunicate Synoicum adareanum, utilizes a convergent carbonyl-based coupling strategy to construct the C1-C24 carbon skeleton. Compound 2 was shown to be a diastereomer of palmerolide C, and the structural revision of the natural product is proposed.

AB - A stereoselective synthesis of the proposed structure of palmerolide C (2), a cytotoxic marine macrolide isolated from the Antarctic tunicate Synoicum adareanum, utilizes a convergent carbonyl-based coupling strategy to construct the C1-C24 carbon skeleton. Compound 2 was shown to be a diastereomer of palmerolide C, and the structural revision of the natural product is proposed.

KW - REVISED STRUCTURES

KW - VINYLOGOUS ALDOL

KW - structure elucidation

KW - natural products

KW - melanoma

KW - CHEMICAL-SYNTHESIS

KW - FRAGMENT

KW - total synthesis

KW - COUPLING-CONSTANTS

KW - macrolide

KW - TUNICATE SYNOICUM-ADAREANUM

KW - ACYCLIC STRUCTURES

KW - NATURAL-PRODUCTS

KW - FORMAL TOTAL-SYNTHESIS

KW - BIOLOGICAL EVALUATION

U2 - 10.1002/chem.201203067

DO - 10.1002/chem.201203067

M3 - Letter

SN - 0947-6539

VL - 18

SP - 14250

EP - 14254

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 45

ER -

Synthesis of the Originally Proposed Structure of Palmerolide C

Abstract

UN SDGs

Keywords

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Projects

RS Uni Research Fellowship Renewal 2010: University Research Fellowship - New Methods and Strategies for the Synthesis of Bioactive Natural Products

Synthesis of Palmerolides EP/F011458/1: Synthesis of the Palmerolides

The Royal Society 516002.K501/kk: Dr G Florence research fellowship application - 2005

Cite this