Toward the total synthesis of spirastrellolide A. Part 3: Intelligence gathering and preparation of a ring-expanded analogue

Alois Fürstner; Bernhard Fasching; Gregory W. O’Neil; Michaël D. B. Fenster; Cédrickx Godbout; Julien Ceccon

doi:10.1039/b707835h

January 1, 2007Chemical Communications

Toward the total synthesis of spirastrellolide A. Part 3: Intelligence gathering and preparation of a ring-expanded analogue

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Key Points

To evaluate reaction pathways for constructing the C25–C26 carbon-carbon bond and assemble a macrocyclic analogue of spirastrellolide A for total synthesis.
Assessed synthetic methodologies to establish the C25–C26 bond within the target skeleton.
Investigated metathesis-driven macrocyclization reactions to construct the macrocyclic ring system.
Identified metathetic coupling conditions capable of forging the core macrocyclic frame.
Synthesized a ring-expanded analogue of spirastrellolide A to establish feasibility for the synthetic endgame.

Implication

Synthetic study evaluates C25–C26 bond-forming strategies for spirastrellolide A, highlighting olefin metathesis for macrocycle assembly.

Abstract

Different methods for the formation of the C.25-C.26 bond of spirastrellolide A () are evaluated that might qualify for the end game of the projected total synthesis, with emphasis on metathetic ways to forge the macrocyclic frame.

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Fürstner et al. (2007) studied this question.

synapsesocial.com/papers/6a999f2f66ec8bd9897ca2ea https://doi.org/10.1039/b707835h

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Toward the total synthesis of spirastrellolide A. Part 3: Intelligence gathering and preparation of a ring-expanded analogue

Key Points

Implication

Abstract

Discussion

Cite This Study

Toward the total synthesis of spirastrellolide A. Part 3: Intelligence gathering and preparation of a ring-expanded analogue

Key Points

Implication

Abstract

Discussion

Cite This Study

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