Synthesis of the Originally Proposed Structure of Palmerolide C

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...

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Bibliographic Details
Published in:Chemistry – A European Journal
Main Authors: Florence, Gordon John, Wlochal, Joanna
Format: Article in Journal/Newspaper
Language:English
Published: 2012
Subjects:
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
Antarctic
The Antarctic
Antarc*
Online Access:https://research-portal.st-andrews.ac.uk/en/researchoutput/synthesis-of-the-originally-proposed-structure-of-palmerolide-c(2745efac-14f6-4fb9-981b-503882ff727f).html
https://doi.org/10.1002/chem.201203067
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Summary: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.

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