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J Am Chem Soc. 2004 Feb 4;126(4):998-9.

Synthesis of amphidinolide T1 via catalytic, stereoselective macrocyclization.

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1
Massachusetts Institute of Technology, Department of Chemistry, Cambridge, Massachusetts 02139, USA.

Abstract

Two nickel-catalyzed reductive coupling reactions of alkynes were instrumental in a modular, stereoselective synthesis of amphidinolide T1 (1). The C13-C21 fragment was prepared from two simple starting materials that were joined in a catalytic alkyne-epoxide fragment coupling operation, whereas an intramolecular aldehyde-alkyne reductive coupling simultaneously formed the final carbon-carbon bond of the macrocycle and established the C13 carbinol configuration with complete selectivity in the desired fashion.

PMID:
14746449
DOI:
10.1021/ja039716v
[Indexed for MEDLINE]
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